Agricultural ureas and isoureas

ABSTRACT

This invention relates to ureas and isoureas which are useful as herbicides and plant growth regulants. In particular, compounds of the instant invention have demonstrated great selectivity.

CROSS-REFERENCE TO RELATED APPLICATION

This is a division of application Ser. No. 662,444, filed Oct. 15, 1984,now U.S. Pat. No. 4,599,103, which is a continuation-in-part ofapplication U.S. Ser. No. 196,267, filed Oct. 22, 1980, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to ureas and isoureas and in particular their useas agricultural chemicals and particularly as herbicides.

U.S. Pat. No. 4,127,405 teaches compounds which are useful forcontrolling weeds in wheat having the formula ##STR1## wherein R₁ is##STR2## R₃ and R₆ are independently hydrogen, fluorine, chlorine,bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms,nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atomsor alkoxy or 1-2 carbon atoms;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbonatoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Y is methyl or methoxy; or their agriculturally suitable salts; providedthat:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ isother than hydrogen and at least two of R₃, R₄, R₆ and R₇ must behydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other thanhydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine ormethyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ mustbe hydrogen.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides, useful as antidiabetic agents: ##STR3## wherein R=H,halogen, CF₃ or alkyl.

Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR4## wherein R is butyl, phenyl or ##STR5## and R₁ is hydrogen ormethyl. When tested for hypoglycemic effect in rats (oral doses of 25mg/100 g), the compounds in which R is butyl and phenyl were mostpotent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR6## Based upon similarity to a known compound, the author predictedhypoglycemic activity for the foregoing compound.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (i), and their use as general orselective herbicides, ##STR7## wherein R₁ and R₂ may independently bealkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

Compounds of Formula (ii), and their use as antidiabetic agents, arereported in J. Drug. Res. 6, 123 (1974), ##STR8## wherein R is pyridyl.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodneeds, such as soybeans, barley, wheat, and the like. The currentpopulation explosion and concomitant world food shortage demandimprovements in the efficiency of producing these crops. Prevention orminimizing the loss of a portion of such valuable crops by killing, orinhibiting the growth of undesired vegetation is one way of improvingthis efficiency.

A wide variety of materials useful for killing, or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. The need exists,however, for still more effective herbicides that destroy or retardweeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formulas I, II, and III andtheir agriculturally suitable salts, suitable agricultural compositionscontaining them, and methods of using them as selective, as well asgeneral herbicides having both pre-emergence and post-emergenceactivity. Some of the compounds are especially useful for controllingweeds in crops such as soybeans: ##STR9## wherein W' is O or S;

A' is H, Cl, Br, C₁ -C₄ alkyl, OCH₃, NO₂ or CF₃ ;

A is ##STR10## where Q is O, S or ##STR11## T is O or ##STR12## whereR^(III) is H, C₁ -C₄ alkyl or C₃ -C₄ alkenyl when Q is O or S then

R^(I) is C₁ -C₆ alkyl; C₃ -C₆ alkenyl; C₃ -C₆ alkynyl; C₂ -C₆ alkylsubstituted with 1-3Cl, F or Br, or one of CN or OCH₃ ; C₃ -C₆ alkenylsubstituted with 1-3Cl; C₃ -C₆ alkynyl substituted with Cl; C₅ -C₆cycloalkyl; cyclohexenyl; cyclohexyl substituted with 1-3CH₃ ; C₄ -C₇cycloalkylalkyl or ##STR13## where R₇ and R₈ are independently H, Cl,CH₃ or OCH₃ ;

n is 0 or 1; and

R₉ is H or CH₃ ; when Q is O then R^(I) is CH₂ CH₂ OR₁₅ ; CH₂ CH₂ CH₂OR₁₅ ; ##STR14## where R₁₅ is C₂ H₅, CH(CH₃)₂, phenyl, CH₂ CH₂ Cl, CH₂CCl₃ ; ##STR15## where R₁₆ is CH₃, C₂ H₅, CH(CH₃)₂, phenyl, CH₂ CH₂ Cl,CH₂ CCl₃, and n' is 2 or 3; CH₂ CN; ##STR16## where R₆ ' is C₁ -C₄alkyl; provided R^(I) has a total of ≦13 carbon atoms; when Q is##STR17## then R^(I) is H; C₁ -C₆ alkyl; --CH₂ CH₂ OR₁₀ ; --CH₂ CH₂ CH₂OR₁₀ ; where R₁₀ is CH₃, CH₃ CH₂, CH(CH₃)₂, or phenyl; C₃ -C₆ alkenyl;C₃ -C₆ cycloalkyl; C₅ -C₆ cycloalkenyl; C₆ cycloalkyl substituted withany one of 1-2OCH₃, 1-3CH₃, --CH₂ CH₃ or CF₃ ; C₄ -C₇ cycloalkylalkyl;--CH₂ CN; --CH₂ CH₂ CN; ##STR18## where R' is H, C₁ -C₄ alkyl, OCH₃, F,Cl, Br, CN, NO₂ or CF₃ ;

R" is H, CH₃, Cl, F or Br;

R₇, R₈ and R₉ are as previously defined;

R₆ is H, C₁ -C₃ alkyl; CH₂ CN; CH₂ CH₂ --CN or --CH₂ --CH═CH₂ and R₆ andR^(I) may be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- or --CH₂CH₂ O--CH₂ CH₂ --;

with the proviso that when R₆ is CH₂ CH₂ CN or CH₂ CN, then R^(I) is CH₂CH₂ CN or CH₂ CN; and R^(I) and R₆ have a total carbon atom count of≦13; and when R^(I) is OCH₃ or OCH₂ CH₃ then R₆ is CH₃ or H;

when A is ##STR19## then R^(II) is H, C₁ -C₆ alkyl; C₃ -C₆ alkenyl;phenyl; benzyl; benzyl or phenyl substituted with 1-2Cl, 1-2OCH₃, 1-2CH₃; C₅ -C₆ cycloalkyl; C₄ -C₇ cycloalkylalkyl with the proviso that when Tis ═N--OR^(III), then R^(II) must be C₁ -C₆ alkyl or C₃ -C₆ alkenyl;

B is ##STR20## where R₄ is H or CH₃ ; W is O or S; R₅ is H, or CH₃ ;with the proviso that either R₄ or R₅ must be H;

R^(IV) is C₁ -C₆ alkyl or C₃ -C₄ alkenyl;

R₁ is ##STR21## where Z is N, CH or C--F; X=H, Cl, --CH₃, --OCH₃ or--OCH₂ CH₃ ;

Y=H; Cl; C₁ -C₄ alkyl; C₁ -C₄ alkyl substituted with --OCH₃, --OC₂ H₅,--CN, --CO₂ CH₃, --CO₂ C₂ H₅, ##STR22## or 1-3 atoms of F, Cl, Br; C₃-C₄ alkenyl; --O--(CH₂)_(n') O--(C₁ -C₃ alkyl) where a' is 2 or 3;##STR23## where L is OH, --NH₂, ##STR24## --NH(C₁ -C₄ alkyl), --N(C₁ -C₄alkyl)₂ or C₁ -C₆ alkoxy; SCN; --N₃ ; NR₁₁ R₁₂ where R₁₁ is H or CH₃ andR₁₂ is H, --OCH₃, C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₄ alkenyl, C₂-C₃ alkyl substituted with OCH₃ or OC₂ H₅, C₁ -C₂ alkyl substituted with--CN, CO₂ H, CO₂ CH₃ or CO₂ C₂ H₅, and R₁₁ and R₁₂ can be taken togetherto form --CH₂ CH₂ CH₂ CH₂ -- or CH₂ CH₂ OCH₂ CH₂ --; --O--R₉ where R₉ isC₁ -C₄ alkyl, C₂ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br,C₁ - C₂ alkyl substituted with cyano, C₃ -C₄ alkenyl, --CH₂ C.tbd.CR₁₃,##STR25## R₁₃ is H, CH₃ or CH₂ Cl; SR₁₄ ; where R₁₄ is C₁ -C₄ alkyl,allyl, propargyl or C₁ -C₂ alkyl substituted with CN; with

the proviso that when X and Y are both H, then R^(I) and R^(II) are lessthan 5 carbons;

X₁ =H, Cl, OCH₃, OCH₂ CH₃ or CH₃ ;

Y₁ =H, OCH₃ or CH₃ ; and

X_(II) =O or CH₂ and further provided that when A contains greater than5 carbon atoms, then Y must contain ≦4 carbon atoms, and theiragriculturally suitable salts.

PREFERRED COMPOUNDS

Preferred for reasons of higher activity and/or lower cost and/orgreater ease of synthesis are compounds:

(1) Of the Generic scope in which B is ##STR26##

More Preferred and in increasing order for reasons of higher activityand/or even lower cost and/or even greater ease of synthesis arecompounds:

(2) Preferred (1) in which W' is sulfur;

(2a) More Preferred (2) in which T is oxygen;

(3) More preferred (2a) in which R₁ is ##STR27##

(4) More Preferred (3) where Q is O or S and R^(I) is C₁ -C₄ alkyl; C₃-C₄ alkenyl; C₃ -C₄ alkynyl; C₂ -C₃ alkyl substituted with CN, OCH₃ or1-3F, Cl or Br; C₃ -C₄ alkenyl substituted with 1-3Cl; C₃ -C₄ alkynylsubstituted with Cl;

(5) More preferred (3) in which Q is oxygen and R^(I) is CH₂ CH₂ OR₁₅ ;CH₂ CH₂ CH₂ OR₁₅ ; ##STR28## where R₁₅ is CH₂ CH₃ ; CH₂ CN; CH₂ OR'₆where R₆ ' is CH₃ or CH₃ CH₂ ; ##STR29##

(6) More Preferred (3) in which Q is ##STR30## and R^(I) is H, C₁ -C₄alkyl, CH₂ CH₂ OR₁₀, CH₂ CH₂ CH₂ OR₁₀ where R₁₀ is CH₃ or CH₃ CH₂ ; C₃-C₄ alkenyl; CH₂ CN; CH₂ CH₂ CN; OCH₃ or OCH₂ CH₃ ; R⁶ is H, C₁ -C₂alkyl, CH₂ CN or CH₂ CH₂ CN and R₆ and R^(I) can be taken together toform --CH₂ --₄.

(7) More Preferred (3) in which R^(II) is H or C₁ -C₃ alkyl;

(8) More Preferred (4), (5), (6) and (7) in which

Z is CH or N;

X is CH₃ or CH₃ O; and

Y is C₁ -C₂ alkyl; C₁ -C₂ alkyl substituted with OCH₃ ; OCH₂ CH₃, CN or1-3 atoms of F, Cl or Br; ##STR31## where L is NH₂, OH, ##STR32##N(CH₃)₂, NHCH₃, C₁ -C₂ alkoxy; SCN; N₃ ; NR₁₁ R₁₂ where R₁₁ is H or CH₃; R₁₂ is H, CH₃, CH₃ CH₂, OCH₃ ; OR₉ where R₉ is CH₃, CH₃ CH₂ ; CH₂CH═CH₂ or CH₂ C.tbd.CH; R₉ is also C₂ alkyl substituted with 1-3F, Cl orBr; CH₃ S;

(9) More Preferred (3) in which A' is H, Cl or Br;

(10) More Preferred (9) in which Q is O or S and R^(I) is C₁ -C₄ alkyl,CH₂ CH═CH₂ or CH₂ CH₂ Cl;

(11) More Preferred (9) in which Q is O and R^(I) is CH₂ CH₂ OCH₃,##STR33## CH₂ OCH₃ or CH₂ OCH₂ CH₃ ;

(12) More Preferred (9) in which Q is ##STR34## and R^(I) is H, C₁ -C₃alkyl, OCH₃ or OCH₂ CH₃ and R₆ is H or C₁ -C₂ alkyl;

(13) More Preferred (9) in which R^(II) is H or CH₃ ;

(14) More Preferred (10), (11), (12) and (13) in which A' is H; Y isCH₃, OCH₃, OCH₂ CH₃, OCH₂ CF₃, OCH₂ CH═CH₂ or OCH₂ C.tbd.CH;

(15) More Preferred (8) in which A is ##STR35## and Q is oxygen orsulfur and R^(I) is CH₃ or CH₂ CH₃ ; Q is ##STR36## and R^(I) is H, CH₃or OCH₃ and R₆ is CH₃ ; R₁ is ##STR37## and Y is CH₃ or OCH₃ ;

(16) More Preferred (15) of Formula I;

(17) More Preferred (15) of Formula II;

(18) More Preferred (15) of Formula III.

Equally More Preferred in increasing order and for reasons of higheractivity and/or even lower cost and/or even greater ease of synthesisare:

(19) Compounds of Preferred 1 in which W' is oxygen;

(20) Compounds of More Preferred (19) in which T is oxygen;

(21) More Preferred (20) in which R₁ is ##STR38##

(22) More Preferred (21) where Q is O or S and R₁ is C₁ -C₄ alkyl; C₃-C₄ alkenyl; C₃ -C₄ alkynyl; C₂ -C₃ alkyl substituted with CN, OCH₃ or1-3F, Cl or Br; C₃ -C₄ alkenyl substituted with 1-3Cl; C₃ -C₄ alkynylsubstituted with Cl;

(23) More Preferred (21) in which Q is oxygen and R^(I) is CH₂ CH₂ OR₁₅; CH₂ CH₂ CH₂ OR₁₅ ; ##STR39## where R₁₅ is CH₂ CH₃ ; CH₂ CN; CH₂ OR₆ 'where R₆ ' is CH₃ or CH₃ CH₂ ; ##STR40##

(24) More preferred (21) in which Q is ##STR41## and R^(I) is H, C₁ -C₄alkyl, CH₂ CH₂ OR₁₀, CH₂ CH₂ CH₂ OR₁₀ where R₁₀ is CH₃ or CH₃ CH₂ ; C₃-C₄ alkenyl; CH₂ CN; CH₂ CH₂ CN; OCH₃ or OCH₂ CH₃ ; R⁶ is H, C₁ -C₂alkyl, CH₂ CN or CH₂ CH₂ CN and R₆ and R^(I) can be taken together toform --CH₂ --₄.

(25) More Preferred (21) in which R^(II) is H or C₁ -C₃ alkyl;

(26) More Preferred (22), (23), (24) and (25) in which

Z is CH or N;

X is CH₃ or CH₃ O; and

Y is C₁ -C₂ alkyl; C₁ -C₂ alkyl substituted with OCH₃ ; OCH₂ CH₃, CN or1-3 atoms of F, Cl or Br; ##STR42## where L is NH₂, OH, ##STR43##N(CH₃)₂, NHCH₃, C₁ -C₂ alkoxy; SCN; N₃ ; NR₁₁ R₁₂ where R₁₁ is H or CH₃; R₁₂ is H, CH₃, CH₃ CH₂, OCH₃ ; OR₉ where R₉ is CH₃, CH₃ CH₂, CH₂CH═CH₂ or CH₂ .tbd.CH; R₉ is also C₂ alkyl substituted with 1-3F, Cl orBr; CH₃ S;

(27) Preferred (21) in which A' is H, Cl or Br;

(28) More Preferred (27) in which Q is O or S and R^(I) is C₁ -C₄ alkyl,CH₂ CH═CH₂ or CH₂ CH₂ Cl;

(29) More Preferred (27) in which Q is O and R^(I) is CH₂ CH₂ OCH₃,##STR44## CH₂ OCH₃ or CH₂ OCH₂ CH₃ ;

(30) More Preferred (27) in which Q is ##STR45## and R^(I) is H, C₁ -C₃alkyl, OCH₃ or OCH₂ CH₃ and R₆ is H or C₁ -C₂ alkyl;

(31) More Preferred (27) in which R^(II) is H or CH₃ ;

(32) More Preferred (28), (29), (30) and (31) in which A' is H; Y isCH₃, OCH₃, OCH₂ CH₃, OCH₂ CF₃, OCH₂ CH═CH₂ or OCH₂ C.tbd.CH;

(33) More Preferred (27) in which A is ##STR46## and Q is oxygen orsulfur and R^(I) is CH₃ or CH₂ CH₃ ; Q is ##STR47## and R^(I) is H, CH₃or OCH₃ and R₆ is CH₃ ; R₁ is ##STR48## and Y is CH₃ or OCH₃ ;

(34) More Preferred (33) of Formula I;

(35) More Preferred (33) of Formula II;

(36) More Preferred (33) of Formula III.

Specifically Preferred for reasons of highest activity and/or lowestcost and/or greatest ease of synthesis are:

methyl3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

methyl3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl3-[[(4-methoxy-6methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl3-[[(4,6-dimethoxy-1,3,5-triazin-2yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylate

methyl2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]3-thiophenecarboxylate

methyl2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylate

methyl2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylate

methyl2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylate

methyl2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylate

methyl2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylate

methyl2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]-3-furancarboxylate

methyl2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylate

methyl2-[[4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylate

methyl2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3furancarboxylate

methyl2-[[(4,6-dimethyl-1,3,5-triazin-2yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylate

methyl2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylate

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(1-pyrrolidinylcarbonyl)-3-thiophenesulfonamide

1-methylethyl3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]2-thiophenecarboxylate

2-propenyl3-[[(4-methoxy-6-methylpyrimidin-2-yl-aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

1-methylethyl3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate.

NOVEL INTERMEDIATES

Also novel and useful for the preparation of compounds of Formulas I, IIand III are compounds of Formulas I', II' and III'. ##STR49## whereinR^(I) is H or M;

M is a cation of an alkalii metal or of a tertiary amine of up to 12carbon atoms;

A', W', B, are as previously defined.

Preferred and in increasing order for reasons of lower cost and/orgreater ease of synthesis and/or higher activity of derived compoundsare those intermediate

(1) Compounds of formulas I', II' and III' in which W' is is sulfur, Bis SO₂ NHCONHR₁, A' is H, Cl or Br and R₁ is ##STR50##

(2) Compounds of Preferred (1) in which X is CH₃ or OCH₃ ; Y is CH₃,OCH₃, OCH₂ CH₃, OCH₂ CF₃, OCH₂ CH═CH₂ or OCH₂ --C.tbd.C--H; Z is CH orN;

(3) Compounds of Preferred (2) in which Y is CH₃ or OCH₃ ; ##STR51## A'is H;

(4) Compounds of Preferred (3) of Formula I';

(5) Compounds of Preferred (4) of Formula II';

(6) Compounds of Preferred (5) of Formula III';

Equally Preferred in increasing order, for reasons of lower cost and/orgreater ease of synethesis and/or higher activity of derived compoundare those intermediate:

(7) Compounds of formulas I', II' and III' in which W' is oxygen; B isSO₂ NHCONHR₁, A' is H, Cl or Br, and ##STR52##

(8) Compounds of Preferred (7) in which X is CH₃ or OCH₃ ; Y is CH₃,OCH₃, OCH₂ CH₃, OCH₂ CF₃, OCH₂ CH═CH₂ or OCH₂ C.tbd.C--H; and Z is CH orN;

(9) Compounds of Preferred (8) in which Y is CH₃ or OCH₃ ; ##STR53## A'is H;

(10) Compounds of Preferred (9) of formula I';

(11) Compounds of Preferred (9) of Formula II';

(12) Compounds of Preferred (9) of Formula III';

Specifically Preferred for reasons of lowest cost and/or greatest easeof synthesis and/or highest activity of desired compounds are:

3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylicacid

3-[[(4,6-dimethylpyrimidin-2yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylicacid

3-[[(4methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylicacid

3[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylicacid

3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiphenecarboxylicacid

3-[[(4-methoxy-6-methyl-1,3,5-triazin-2yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylicacid

3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

3-[[(4,6-ddimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

3-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-furancarboxylicacid

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonylaminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-thiophenecarboxylicacid

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid

2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid

2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid

2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-3-furancarboxylicacid.

Also novel and useful for the preparation of compounds of Formulas I, IIand III are compounds of Formulas II", I" and III" ##STR54## wherein Wis oxygen or sulfur;

W' is oxygen or sulfur;

A' is H, Cl, Br, C₁ -C₄ alkyl, OCH₃, NO₂ or CF₃ ;

R^(I) is C₁ -C₆ alkyl; C₃ -C₆ alkenyl; C₃ -C₆ alkynyl; C₂ -C₆ alkylsubstituted with Cl, CN or OCH₃ ; C₃ -C₆ alkenyl substituted with 1-3Cl; C₃ -C₆ alkynyl substituted with Cl; C₅ -C₆ cycloalkyl; cyclohexenyl;cyclohexyl substituted with 1-3 CH₃ ; C₄ -C₇ cycloalkylalkyl or##STR55## where R₇ and R₈ are independently H, Cl, CH₃ or OCH₃ ;

n is0 or 1; and

R₉ is H or CH₃ ; --CH₂ CH₂ OR₁₅, CH₂ CH₂ CH₂ OR₁₅, ##STR56## where R₁₅is C₂ H₅, CH(CH₃)₂, phenyl, CH₂ CH₂ Cl, CH₂ CCl₃ ; --CH₂ CH₂ O--_(n),R₁₆, ##STR57## R₁₆ where R₁₆ is CH₃, C₂ H₅, CH(CH₃)₂, phenyl, CH₂ CH₂Cl, CH₂ CCl₃, and n' is 2 or 3; CH₂ CN; ##STR58## where R₆ ' is C₁ -C₄alkyl; provided R^(I) has a total of ≦13 carbon atoms.

Preferred in increasing order for reasons of lower cost and/or greaterease of synthesis and/or higher activity of desired compounds are thoseintermediate:

(1) Compounds of formulas I", II" and III" in which W' is sulfur; W isoxygen; A' is H, Cl or Br; and R^(I) is C₁ -C₄ alkyl; CH₂ CH═CH₂ ; orCH₂ CH₂ Cl; CH₂ CH₂ OCH₃ ; or ##STR59##

(2) Compounds of Preferred (1) in which R^(I) is CH₃ or CH₂ CH₃ ; A^(I)is H;

(3) Compounds of Preferred (2) of Formula I";

(4) Compounds of Preferred (2) of Formula II";

(5) Compounds of Preferred (2) of Formula III".

Equally Preferred in increasing order for reasons of lower cost and/orgreater ease of synthesis and/or higher activity of derived compoundsare those intermediate:

(6) Compounds of formulas I", II", and III" in which W' is oxygen; W isoxygen; A' is H, Cl or Br;

(7) Compounds of Preferred (6) in which R^(I) is CH₃ or CH₂ CH₃ ; A^(I)is H;

(8) Compounds of Preferred (7) of Formula I".

(9) Compounds of Preferred (7) of Formula II".

(10) Compounds of Preferred (7) of Formula III".

Specifically Preferred for reasons of lowest cost and/or greatest easeof synthesis and/or highest activity of desired compounds are:

methyl 3-(isocyanatosulfonyl)-2-thiophenecarboxylate

methyl 2-(isocyanatosulfonyl)-3-thiophenecarboxylate

methyl 4-(isocyanatosulfonyl)-3-thiophenecarboxylate

methyl 3-(isocyanatosulfonyl)-2-furancarboxylate

methyl 2-isocyanatosulfonyl)-3-furancarboxylate

methyl 4-(isocyanatosulfonyl)-3-furancarboxylate.

SYNTHESIS

Many of the compounds of Formulas I-III are prepared as shown inEquation 3 by the reaction of an appropriately substitutedalkoxycarbonylthiophene or furan sulfonylisocyanate orsulfonylisothiocyanate with an appropriate aminopyrimidine oraminotriazine. These compounds of Formulas I-III can be converted toother compounds of Formulas I-III as will be shown in subsequentequations.

The novel sulfonylisocyanates are important intermediates for thepreparation of the compounds of this invention. Their synthesis isdescribed in Equations 1 and 2. ##STR60##

A mixture of the appropriate sulfonamide, e.g. an2-alkoxycarbonyl-3-thiophene sulfonamide IV such as the methyl ester,which is known in the art, an alkyl isocyanate such as butyl isocyanateand a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) inxylene or other inert solvent of sufficiently high boiling point(e.g. >135°) is heated to approximately 130°-150° C. Phosgene is addedto the mixture until an excess of phosgene is present as indicated by adrop in the boiling point. After the mixture is cooled and filtered toremove a small amount of insoluble by-products, the solvent and alkylisocyanate are distilled off in-vacuo leaving a residue which is thecrude sulfonyl isocyanate V. In Equation 1,

A', W' and CO₂ R^(I) are as defined previously for structures I", II"and III".

The novel sulfonylisothiocyanate intermediates of Formula Va, preparedaccording to Equations 2 and 2', are useful for the preparation ofcompounds of Formulas I-III where W=S. ##STR61##

The alkoxycarbonyl substituted sulfonamide is dissolved indimethylformamide (DMF) with an equivalent amount of carbon disulfideand two equivalents of potassium hydroxide are added portionwise at roomtemperature. The mixture is stirred for 1-8 hours and diluted withethylacetate, ethyl or similar aprotic solvent to cause the dipotassiumsalt of the dithiocarbamic acid to precipitate. The salt is isolated,dried and suspended in an inert solvent such as xylene, benzene, carbontetrachloride or methylene chloride. Phosgene is added to the stirredsuspension at below room temperature and the mixture stirred for 1-3hours. In place of phosgene, a chloroformic ester (e.g. methylchloroformate), phosphorous pentachloride, sulfuryl chloride or thionylchloride can be used.

The sulfonylisothiocyanate which is formed is usually soluble in thesolvent and is isolated by filtering off the insoluble potassiumchloride and concentrating the filtrate. These isothiocyanates tend tobe unstable and dimerize readily, (Equation 2') however, the dimers canbe used.

Alternate routes to prepare sulfonylisothiocyanates are described by M.O. Lozinskii et al. in Organic Compounds: Reactions and Methods, Ed. byB. A. Kazanskii et al., Vol 22, p 188-197, Plenum Press, 1973 (Engl.Trans.) ##STR62## in the same manner as the parent isothiocyanates forthe purposes of this invention.

The synthetic method chosen for the preparation of compounds of FormulasI-III depends largely on the substituents of QR^(I) and R₄. As shown inEquation 3, compounds of Formulas I-III, wherein R^(I) or A' are asdefined for Equation 1, are conveniently prepared by reacting anappropriately substituted carbonyl thiophene or furan sulfonylisocyanate or isothiocyanate of Formula V with an appropriatelysubstituted aminopyrimidine or aminotriazine of Formula VI: ##STR63##

The reaction of Equation 3 is best carried out in inert aprotic organicsolvents such as methylene chloride, tetrahydrofuran or acetonitrile, atambient pressure and temperature. The mode of addition is not critical;however, it is often convenient to add the sulfonyl isocyanate orisothiocyanate to a stirred suspension of amine VI. Since suchisocyanates and isothiocyanates are liquids, low melting solids or arereadily soluble in solvents such as those listed above, their additioncan be easily controlled.

The reaction is generally exothermic. In some cases, the desired productis soluble in the warm reaction medium and on cooling crystallizes inpure form. Other products which are soluble in the reaction medium areisolated by evaporation of the solvent, trituration of the solid residuewith solvents such as 1-chlorobutane or ethyl ether, and filtration.

As shown in Equation 4, compounds of Formulas I-III, wherein W is S, Aand A' are as previously defined and R₅ is H, are altervatively preparedby the reaction of an appropriately substituted thiophene or furansulfonamide with the appropriate triazine or pyrimidine isothiocyanateof Formula VIa. ##STR64##

The reaction of Equation 4 is best carried out by dissolving orsuspending the sulfonamide and isothiocyanate in a polar solvent such asacetone, acetonitrile, ethyl acetate or methylethylketone, adding anequivalent of a base such as potassium carbonate and stirring themixture at a temperature from ambient up to the reflux temperature forone to twenty-four hours. In some cases, the product precipitates fromthe reaction mixture and can be removed by filtration. The product isstirred in dilute mineral acid, filtered and washed with cold water. Ifthe product does not precipitate from the reaction mixture, it can beisolated by evaporation of the solvent, trituration of the residue withdilute mineral acid and filtering off the insoluble product.

The heterocyclic isothiocyanates which are used in the procedure ofEquation 4 are prepared, for example, according to the method of JapanPatent Application Pub: Kokai No. 51-143686, June 5, 1976, or that of W.Abraham and G. Barnikow, Tetrahedron 29, 691-7 (1973).

As shown in Equation 5, compounds of Formulas I-III, wherein A, A', R₁,W', and R₅ are as defined previously, and W is O, can be prepared bymethylation of salts VII wherein M is an alkali metal cation such assodium (derived from compounds of Formula I-III wherein R₄ is hydrogen):##STR65## D being an incipient anion and n being an integercorresponding to the valence of D.

The reaction of Equation 5 is best carried out in aprotic organicsolvents such as tetrahydrofuran, dimethylformamide, ordimethylacetamide, at ambient pressure and temperature. Methylatingagents VIII such as dimethyl sulfate or methyl iodide, can be employed.The desired product can be isolated by pouring the reaction mixture intowater and filtering off the precipitated solid.

As shown in Equation 6, compounds of Formulas I-III wherein A, A', R₁,W', and R₅ are as defined for Equation 5, and W is O or S, can also beprepared by the reaction of an appropriately substitutedsulfonyl-N-methylcarbamyl chloride or sulfonyl-N-methylthiocarbamylchloride of Formula IX with an appropriate aminopyrimidine oraminotriazine of Formula VI; ##STR66##

The preparation of ureas and thioureas, like those of Formula Ic, fromamines and carbamyl chlorides and thiocarbamyl chlorides is well knownto the art. The reaction can best be carried out by adding equivalentamounts of chloride IX and amine VI to an inert organic solvent, such astetrahydrofuran, xylene, or methylene chloride, in the presence of anacid acceptor, such as triethylamine, pyridine, or sodium carbonateemploying temperatures from 20°-130°. Soluble products can be isolatedby filtering off the precipitated salt and concentration of thefiltrate. Insoluble products can be filtered off and washed free ofsalts with water.

The chlorides of Formula IX can be prepared by phosgenation orthiophosgenation of N-methylsulfonamide salts. The sulfonamide salt isadded to an excess of phosgene or thiophosgene in an inert organicsolvent, such as tetrahydrofuran, toluene, or xylene, whereupon, afterremoval of the excess phosgene, the chloride IX can be isolated orreacted in situ with the amine VI.

The esters of Formulas I-III hydrolyze to the parent acid as shown inEquation 7. Alkali metal base catalyzed hydrolysis in aqueous methanolproduces the alkali metal carboxylate from which the carboxylic acid isobtained by treatment with mineral acids such as HCl: ##STR67##

The reaction of Equation 7 is best carried out in a solution containingthe compound being hydrolyzed, 2 to 10 parts of methanol, 10-50 parts ofwater and 2-10 equivalents of a base such as sodium or potassiumhydroxide containing the temperature at 30°-90° C. for 3-24 hours. Thereaction yields the soluble alkali metal salt of the carboxylic acid,which is suitable for the purposes of this invention. Conversion ofthese salts to the acid form is easily carried out by addition to thereaction medium of strong mineral acids, such as hydrochloric orsulfuric acid, causing the desired carboxylic acids to precipitate fromsolution.

The acids of Formula Ie prepared as in Equation 7 wherein W is O can beconverted to compounds of this invention where R^(I) is a higher alkylor substituted hydrocarbyl group, as already disclosed herein, by thereaction of salts of the parent acid with R^(I) -halogen as shown inEquation 8. ##STR68##

The reaction of Equation 8 is of use where the intermediate compoundR^(I) -halogen contains a readily replaceable halogen as is the case forsubstituted or unsubstituted allylic or benzylic halides,α-halonitriles, or α-halocarbonyl compounds.

The procedure of Equation 8 is best carried out in inert polar solventssuch as tetrahydrofuran, acetonitrile or acetone by combining theappropriately substituted carboxylic acid and base such as triethylamineor 1,4-diaza[2,2,2]bicyclooctane adding the appropriate halide andheating the mixture to reflux with stirring for 1 to 16 hours. Thereaction mixture can be evaporated to dryness and the residue trituratedwith water, filtered and washed with water to separate the desiredproduct from the water soluble salt.

The procedure of Equation 8 can also be used for the synthesis ofcompounds wherein R^(I) -halogen of Equation 8 is of a less reactivespecies than described above. In these cases, the silver salt of thecarboxylic acid is used rather than the amine salt. The silver saltwhich is precipitated by adding silver nitrate to an aqueous solution ofthe sodium salt of the acid of Formula Ie is combined with theappropriate R^(I) -halide using the same solvents and conditions asshown above for the amine salt.

When Q is NR₆, the compounds can be prepared from the esters of thisinvention where R^(I) is C₁ -C₄ (preferably C₁) by the reaction of theesters with dialkylaluminum-N-alkylamide derivatives according toEquation 9; R^(I), A', W', R₁, R₄, R₅ and R₆ being as previouslydefined. ##STR69##

The intermediate alkylaminoaluminum compounds prepared according to A.Basha, M. Lipton and S. W. Weinreb, Tetrahedron Letters 4171 (1977), arecomingled with a suspension of the esters in toluene or similar inertsolvent and the mixture is refluxed for one to six hours. The productcan be isolated by evaporation of the solvent, addition of methylenechloride and aqueous hydrochloric acid to decompose the residualreaction mass and extracting the desired product into methylenechloride. Evaporation of the methylene chloride yields the desiredproduct in sufficiently pure form for the purpose of this invention.

Compounds of Formula X, wherein Q is ##STR70## A', W' and R₄ are aspreviously defined in the general formula, which are useful asintermediates in Equation 4, are prepared as shown in Equation 10.##STR71## The conditions described for Equation 8 are suitable for theconversion of the esters of Formula IVa to the carboxamides as shown inEquation 10.

The products of Equation 10 are especially useful for the preparation ofcompounds of Formulas I-III wherein Y has an ester substituent CO₂ (C₁-C₆), by the route described in Equation 4.

When Q is S, these compounds can be prepared from the esters of thisinvention wherein QR^(I) is O(C₁ -C₄ alkyl) (preferably C₁) by thereaction of the esters with the appropriate dialkylaluminumalkylthiolate according to Equation 11. ##STR72##

The intermediate aluminum thiolates can be prepared according to R. P.Hatch and S. W. Weinreb, Journal of Organic Chemistry, Vol. 42, 3960(1977). The reaction of the thiolate with the ester of this invention isbest carried out in a neutral solvent such as toluene or xylene atreflux for one to three hours. Best results are obtained when thealuminum thiolate compound is present in excess of the stoichiometricamount required.

Sulfonamides of Formula IVc are also converted from carboxylic acidesters to the thiolesters as shown in Equation 12 according to themethod of R. P. Hatch and S. W. Weinreb as described for Equation 11wherein R^(I), A', W' and R₄ are as previously defined. ##STR73## Theconditions described for Equation 11 are suitable for the conversion ofthe sulfonamides of Formula IVc as shown in Equation 12.

The products obtained by the procedure of Equation 12 are especiallyuseful for the preparation of compounds of formula I-III where Y has asubstituent (CO₂ C₁ -C₆) by the route described for Equation 4 and Q=S.

An alternate route to prepare compounds where R^(I) is bonded to Q (Q=O)at a secondary carbon involves the reaction of the appropriatedialkylaluminum alcoholate and an ester of this invention wherein R^(I)is a lower primary alkyl group, preferably methyl, according to Equation13. ##STR74##

The reaction is carried out in a neutral solvent such as toluene with aboiling point sufficiently high to bring about the desired reactionduring reflux. The dialkylaluminum alcoholate being present in greaterthan an equivalent amount to the ester for best yields. After refluxingfor 1-15 hours, the reaction mixture is decomposed with dilutehydrochloric acid and the product extracted into methylene chloride.Evaporation of the methylene chloride yields the desired compoundsufficiently pure for the purposes of this invention. The product can betriturated with a solvent, e.g. 1-chlorobutane to remove impurities.

Ketones where A is ##STR75## and A', W', W, R₁, R₄ and R₅ are as definedby the scope of this invention, are prepared according to Equation 14,from the carboxylic acids of Formula Ie whose preparation is describedin Equation 7. ##STR76##

The reaction of an organolithium compound with a carboxylic acid toyield a ketone as in Equation 14 is described in the work of H. Gilmanand P. R. Van Ess, JACS, 55, 1258 (1933); H. Gilman, W. Langham and F.W. Moore, ibid., 62 (1940); C. Tegner, Chem. Scand., 6, 782 (1952); J.F. Arens and D. A. Van Dorp, Rec. Trav., 65 338 (1946); 66, 759 (1947);C. H. Depuy, G. M. Dappen, K. L. Eilers and R. A. Klein, J. Org., 29,2813 (1964).

An excess of the organolithium compound in a suitable solvent such asdiethyl ether, hexane, pentane or benzene is added to a solution orslurry of XI in a similar solvent at temperatures between -100° and 0°C. The mixture is allowed to warm to room temperature and stir for 30minutes. Aqueous acid is then added and the ketosulfonamide extractedinto a suitable solvent to free it from salts followed by evaporation ofthe solvent.

The synthesis of a wide variety of organolithium compounds by manydifferent procedures is known in the art. A summary of methods withbibliography is contained in Organo-Metallic Compounds, G. E. Coates,John Wiley and Sons, 1960, p. 3-21.

Oximes of the ketones of Formula XI, for example, can be prepared fromthe appropriate hydroxylamine derivative, wherein R^(III) is aspreviously defined, and the ketone of Formula XI according to Equation15. ##STR77##

A procedure such as that described in Preparation Organic Chemistry byG. Hilgetag and A. Martini, Ed., John Wiley and Sons, p. 513 is suitablefor the preparation of the oximes of this invention.

Compounds of Formulas I-III wherein B is ##STR78## and W is O, areprepared by the sequence of reactions shown in Equation 16. ##STR79##

The compounds of Formula XVII are prepared by adding an appropriatecarbon tetrahalide to a solution of a compound of Formula XII andtriphenyl phosphine in an inert aprotic solvent such as acetonitrile atabout -10° to 25° and stirring at the designated temperature for 10 to48 hours. The carbamimidoyl halides of Formula XVI thus formed may beisolated by passing the reaction solution through a silica gel column toremove the triphenyl phosphine oxide and removal of the solvent byevaporation under reduced pressure.

The compounds of Formula XVI can be converted to the correspondingcompounds of Formula XVII by treating reaction mixture with a metalalkoxide, NaOR^(III), at -10° to 25° and stirring at ambient temperaturefor 2 to 24 hours. The crude products of Formula XVII are isolated byfiltering off the precipitated metal halide and removing the solvent byevaporation under reduced pressure. Further purification may beaccomplished by recrystallization or by column chromatography oversilica gel.

It will be understood that the compounds of Formula XVI are notnecessarily converted directly to the compounds of Formula XVII, but mayfirst form the carbodiimides of Formula XVIII. ##STR80##

Many compounds, particularly compounds in which the heterocyclic moietyis pyrimidinyl, may be prepared by the sequence of reactions shown inEquation 17. ##STR81##

The compounds of Formula XIX are prepared according to the procedure orR. Gompper and W. Hagele in Chemische Berichte 99, 2885-2899 (1966).

The compounds of Formula XX are prepared from the compounds of FormulaXIX with sulfuryl chloride in an inert organic solvent such as methylenechloride or chloroform at temperatures between -10° and 80°. They areisolated by removing the solvent under reduced pressure, and can be usedwithout further purification.

The compounds of Formula XXI are prepared in the following manner: Thelithium salt of the appropriate aminoheterocycle is prepared from theaminoheterocycle with n-butyl lithium in a solvent such astetrahydrofuran. To this salt solution is added the compound of FormulaXX in tetrahydrofuran at a temperature of about -10° to 10°. Thereaction mixture is then stirred at about 0°-10° for 1/2-2 hours and atambient temperature for 1/2-4 hours. The products of Formula XXI areisolated by filtering off the inorganic salts and removing the solventunder reduced pressure. Further purification can be done byrecrystallization or by column chromatography on silica gel using asuitable eluent such as ethyl acetate.

As shown in Equation 18, the compounds of Formula XXIV, wherein##STR82## and W=S can be prepared by reacting an appropriatelysubstituted carbamimidothioic acid salt of Formula XXII with analkylating agent of Formula XXIII. ##STR83## wherein D is a sulfate orhalogen, such as Cl, Br or I; M is an alkali or alkaline earth metal,and n is an integer corresponding to the valence of D.

The reaction is best carried out in inert aprotic organic solvents suchas tetrahydrofuran or diethyl ether at temperatures between 25° and 100°C. and ambient pressure. The mode of addition is not critical; however,it is often convenient to add the alkylating agent in solution to astirred suspension of the salt of Formula XXII. The product is isolatedby evaporation of the solvent and can be purified by recrystallizationfrom a solvent such as acetonitrile or ethanol.

The metal salts of Formula XXII can be prepared by treating thecorresponding sulfonylthiourea with a solution of an alkali metal oralkaline earth metal salt having an anion sufficiently basic to theproton (e.g. hydroxide, alkoxide, carbonate or hydride).

When Z is N, the preferred procedure for the preparation of compounds ofFormula XXIV is that shown in Equation 19. ##STR84##

A compound of Formula XXV is treated with an alkali metal (M') salt ofthe appropriately substituted heterocyclic amine at temperatures of 0°to 100° C. in a solvent such as dimethylformamide, dimethylsulfoxide oran ethereal solvent, such as tetrahydrofuran.

Compounds of Formula XXV can be prepared according to the procedure ofChem. Ber. 99, 2885 (1966).

Compounds of Formulas I-III wherein Y of group R₁ contains ##STR85## andL is OH can be prepared according to the procedure of Equation 20wherein A', W', X, R₄, W and R₅ are as defined previously; and Q' is C₁-C₄ alkyl, OCH₂, OCH₂ CH₂, ##STR86## where R₁₁ is as previously defined.##STR87##

The reaction of Equation 20 is best carried out by suspending thecompound being hydrolyzed in 10 to 100 parts of water with enough of abase such as sodium hydroxide or potassium hydroxide to obtain a pH 10to 14, ideally a pH of 12, heating until a clear solution is obtainedand then adjusting the pH to 1-3, preferably 3. The product is thuscaused to precipitate in some instances and can be removed by filtrationor it can be extracted into a polar organic solvent such as methylenechloride and isolated by evaporation of the solvent.

Thiophene derivatives with sulfamoyl and alkoxycarbonyl substituents onadjacent carbon atoms are prepared by the methods taught by O. Hromatkaand D. Binder, U.S. Pat. No. 4,028,373 and P. A. Rossy et al., U.S. Pat.No. 4,143,050. The analogous furan derivatives are prepared similarly oras taught in Belgian Pat. No. 871,772.

Alternate methods of preparation of thiophene and furan sulfonamideswith alkoxycarbonyl substituents adjacent to the sulfonamide arepreferable in certain circumstances. For example, if one of theα-carbons is not substituted, chlorosulfonation of a furan or thiophenemay give the undesired substituted sulfonyl chloride or a mixture ofisomers. Regio-specific introduction of substituents may be achieved inmany cases via ring metalation reactions. The use of such reactions hasbeen reviewed by H. Gschwend and H. Rodriguez in "Organic Reactions",Vol. 26 (John Wiley & Sons, Inc., New York, 1979). Using these methods,the 2-lithio-3-furancarboxylates or -thiophenecarboxylates may begenerated from the corresponding acid and two equivalents of analkyllithium in an inert, aprotic solvent such as an ether solvent.These intermediates are described in ##STR88## Tetrahedron Letters 5051(1980) and references therein. Treatment of these organolithium specieswith sulfur dioxide afford the corresponding 2-sulfinate-3-carboxylatesalts which are conveniently isolated by evaporation of the solvent. Thelithium sulfinates are converted to the sulfonamides by reaction with anexcess of chloramine in aqueous solution and isolated by acidificationand extraction ##STR89## into an organic solvent. Esterification of theresulting acids under standard conditions (e.g., methanol, sulfuric acidcatalyst, 25°-65° C., 1-24 h) yield the appropriate alkoxycarbonylsulfonamides.

Other isomeric furan and thiophene sulfonamides may be prepared througha sequence of these metalation reactions as shown below. The reaction of3-bromofurans or -thiophenes with alkyllithium reagents at lowtemperatures (preferably below -40°) in an aprotic, inert solvent affordthe corresponding 3-lithiofurans and -thiophenes via halogen-metalexchange. These may be quenched with sulfur dioxide to yield the3-sulfinic acid salts. They may be subsequently ##STR90## converted tosulfonyl chlorides with a chlorinating agent, conveniently with areagent such as N-chlorosuccinimide (NCS) in a suitable solvent such asacetic acid, preferably at ambient temperature. The ##STR91##3-t-butylsulfonamide is then prepared upon reaction of the sulfonylchloride with excess t-butylamine. Reaction of the sulfonamide with##STR92## two equivalents of an alkyllithium, as described above for the3-carboxylic acids, yield specifically the 2-lithio intermediates whichare quenched with carbon dioxide to afford the 2-carboxylic acid salts.Esterification of the carboxylic acid and removal of the t-butyl groupmay be accomplished in one reaction by heating the above products in analcohol solvent with acid catalyst (e.g. methanol, sulfuric acid).##STR93##

For 3,4-disubstituted furan and thiophene sulfonamides, a modificationof the above sequence is appropriate. A4-bromo-3-t-butylsulfamoylthiophene or furan intermediate may beprepared by the methods outlined above beginning with the 3,4-dibromocompound. Reaction of these sulonamides with ##STR94## two equivalentsof alkyllithium in preferably an ether solvent at low temperature(preferably less than -40°) will afford the 3-lithio species viahalogen-metal exchange. These may be subsequently quenched with carbondioxide to yield the carboxylic acids which are then converted to thefree sulfonamide-esters as outlined above for the 2,3-disubstitutedisomers.

Compounds of structure XXIX wherein A is an aldehyde group and A' doesnot equal --NO₂ are prepared by the procedure of Equation 21. ##STR95##

Following the procedure of R. Kanazawa and T. Tokoroyama, Synthesis, 526(1976), a solution of sodium bis-(2-methoxyethoxy)aluminum hydride inTHF is reacted with one equivalent of morpholine. To this solution at-40° C. is added a methyl ester of Formula XXVIII and the solution isallowed to warm to 25° C. The product is isolated by addition of aqueousacid and extraction into ether or methylene chloride. Evaporation of thesolvent and crystallization or column chromatography on silica gelaffords the aldehyde XXX.

Aldehydes of Formula XXX may also be prepared from the esters bytreatment with diisobutylaluminum hydride according to the procedures ofE. Winterfeldt, Synthesis, 617 (1975).

Compounds of Formulas I, II and III may also be prepared by the reactionof the appropriately substituted thiophene or furan sulfonamides withthe appropriate heterocyclic isocyanate using the methods described inco-pending applications U.S. Ser. No. 098,725 and U.S. Ser. No. 098,722,filed Nov. 30, 1979.

The synthesis of heterocyclic amines has been reviewed in "The Chemistryof Heterocyclic Compounds" a series published by Interscience Publ., NewYork and London. 2-Aminopyrimidines are described by D. J. Brown in thePyrimidines, Vol. XVI of this series. The 2-amino-1,3,5-triazines arereviewed by K. R. Huffman and in the Triazines of this same series. Thesynthesis of triazines are also described by F. C. Schaefer, U.S. Pat.No. 3,154,547 and By K. R. Huffman and F. C. Schaeffer, J. Org. Chem.28, 1816-1821 (1963).

The preparation of the aminoheterocycles described by Formula XXX variesaccording to the definition of Y₁ and X_(II). ##STR96##

Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc. 69, 3072 (1947)describe the preparation of6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-amine by the followingsequence of reactions. ##STR97##

Similarly, 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine can beprepared by the condensation of 2-acetylcyclopentanone with guanidinecarbonate, but preferably under acidic conditions, removing the waterformed. ##STR98##

Shrage and Hitchings, J. Org. Chem. 16, 1153 (1951) describe thepreparation of 5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-amine by thefollowing sequence of reactions ##STR99##

5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine can be prepared by themethod of Braker et al., J. Am. Chem. Soc. 69, 3072 (1947), using5,6-dihydro-4-hydroxyfuro[2,3-d]pyrimidin-2-amine [Svab, Budesinski andVavrina, Collection Czech. Chem. Commun. 32, 1582 (1967)]. ##STR100##

Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc. 63, 2188 (1941),describe the preparation of 6,7-dihydro-5H-cyclopentapyrimidin-2-amineby the following sequence of reactions. ##STR101##

Fissekis, Myles and Brown, J. Org. Chem. 29, 2670 (1964), describe thepreparation of 2-amino-4-hydroxy-5-(2-hydroxyethyl)pyrimidine which canbe converted to 5,6-dihydrofuro[2,3-d]pyrimidin-2-amine by dehydration.##STR102##

Agriculturally suitable salts of compounds of Formulas I-III are alsouseful herbicides and can be prepared by a number of ways known to theart. For example, metal salts can be made by treating compounds ofFormulas I-III with a solution of alkali or alkaline earth metal salthaving a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonateor hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formulas I-III can also be prepared by exchange ofone cation to another. Cationic exchange can be effected by directtreatment of an aqueous solution of a salt of a compound of FormulasI-III (e.g., alkali metal or quaternary amine salt) with a solutioncontaining the cation to be exchanged. This method is most effectivewhen the desired salt containing the exchanged cation is insoluble inwater, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formulas I-III (e.g., an alkali metal or quaternaryamine salt) through a column packed with a cation exchange resincontaining the cation to be exchanged. In this method, the cation of theresin is exchanged for that of the original salt and the desired productis eluted from the column. This method is particularly useful when thedesired salt is water soluble, e.g., a potassium, sodium or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formulas I-III with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade.

The desired product is underscored at the top of each example.

EXAMPLE 1 2-Methoxycarbonyl-3-thiophenesulfonyl isocyanate

A mixture containing 22.1 g ofmethyl-3-sulfamoylthiophene-2-carboxylate, 9.9 g of n-butyl isocyanate,0.3 g of 1,4-diaza[2,2,2]bicyclooctane and 150 ml of dry xylene wasplaced in a 4 neck round bottom flask equipped with a gas inlet tube,mechanical stirrer, thermometer and dry ice cooled reflux condenser.This mixture was heated to 135° C. and phosgene was passed into theflask so that after several minutes, the reflux temperature dropped to120°. The phosgene addition was halted until the temperature rose to130° and then additional phosgene was added to cause the temperature todrop again to 120°. The phosgene addition cycle was repeated until thereflux temperature of the reaction mixture remained at 120° with nofurther phosgene addition.

Cooling the reaction mixture caused a small amount of a precipitate toform which was removed by filtration and the filtrate was concentratedin-vacuo to yield an oil which showed a strong absorption peak in theinfrared region at 2200 cm⁻¹ consistent for the desired sulfonylisocyanate. This highly reactive intermediate was used without furtherpurification.

EXAMPLE 2 Methyl3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

To 1.23 g of 2-amino-4,6-dimethyl pyrimidine in 30 ml of anhydrousacetonitrile was added with stirring 2.7 g of2-methoxycarbonyl-3-thiophenesulfonylisocyanate. The mixture was heatedto the boiling point, whereupon all of the insoluble material dissolvedand the mixture was allowed to cool. After stirring for two hours themixture was filtered to remove the desired product which hadprecipitated as a white solid. After washing with anhydrous ethyl etherthe product melted at 191°-193° with decomposition and showed absorptionpeaks by nuclear magnetic resonance at 3.8 ppm for the methoxy group,2.44 ppm for the two methyl groups on the pyrimidine ring, a peak at 7.0consistent for the hydrogen in the pyrimidine ring and a peak at 7.42for the hydrogens on the thiophene ring. The infrared absorptionspectrum showed absorption peaks at 1720 and 1700 cm⁻¹ consistent forthe two carbonyl groups present in the desired product.

EXAMPLE 3 Methyl 3 [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

To 1.5 g of 2-amino-4,6-dimethoxypyrimidine in 30 ml of anhydrousacetonitrile was added 2.7 g of 2-methoxycarbonyl-3-thiophenesulfonylisocyanate with stirring at ambient temperature. All of the solidreactant dissolved and after twenty minutes of stirring a precipitatestarted to form. After two hours the mixture was filtered and the solidwhich was washed with anhydrous ethyl ether, melted at 191°-193°. Thesolid showed peaks by nuclear magnetic resonance spectroscopy at 4.0 ppmand 3.8 ppm for the methoxy groups, 6.0 ppm for the H of pyrimidine and7.6 ppm for the hydrogens on thiophene. The infrared absorption spectrumshowed absorption peaks at 1730 and 1700 cm⁻¹ consistent for the twocarbonyl peaks in the desired product.

EXAMPLE 4 Methyl3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

To 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrousacetonitrile was added at ambient temperature, with stirring 3.6 g of2-methoxycarbonyl-3-thiophenesulfonylisocyanate. The mixture was heatedto the boiling point and then allowed to cool to ambient temperature.After stirring for sixteen hours the precipitate present in the mixturewas filtered off and washed with anhydrous ethyl ether. The product thusobtained which melted at 165°-173° showed absorption peaks by infraredspectroscopy at 1720 and 1700 cm⁻¹, consistent for the carbonyl groupsin the desired product.

EXAMPLE 5 Methyl3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

To 1.23 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 30 ml of anhydrousmethylene chloride was added with stirring 2.7 g of2-methoxycarbonyl-3-thiophenesulfonylisocyanate. The mixture was heatedto the boiling point and allowed to cool and stir at ambient temperaturefor sixteen hours. The solid thus obtained was removed by filtration toyield 2.3 g of the crude desired product melting at 158°-178°. Theproduct showed peaks at 1720 and 1710 cm⁻¹, by infrared absorptionspectroscopy, consistent for the desired product.

EXAMPLE 6 Methyl3-[[(5,6-dimethyl-1,2,4-triazinyl-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate

To 1.2 g of 3-amino-5,6-dimethyl-1,2,4-traizine in 30 ml of anhydrousmethylene chloride was added with stirring 2.7 g of2-methoxycarbonyl-3-thiophenesulfonylisocyanate. After stirring for 16hours at ambient temperature the solution was filtered to remove someinsoluble material and the filtrate evaporated to dryness. The residuethus obtained was triturated with ethyl ether and the insoluble productfiltered to yield 2.9 g of the desired compound melting at 129° withdecomposition. Infrared analysis of this product showed absorption peaksat 1730 and 1700 cm⁻¹ as expected for the desired product.

EXAMPLE 7 3-[[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophene carboxylic acid

A solution of 1.0 g of methyl3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylatein 10 ml of ethanol and 1 ml of 50% sodium hydroxide in water wasstirred overnight at room temperature. To this was added ice-water andaqueous hydrochloric acid until acidic, and the precipitate was filteredand washed first with acetone and then with methylene chloride. Theproduct, 0.8 g, melted at 127°.

EXAMPLE 81-[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]thiene-2-ylcarbonyl]pyrrolidone

To 2.5 ml of a 2M-solution of trimethylaluminum in toluene was added 20ml of methylene chloride and 400 μl of pyrrolidine. To this solution wasadded 0.66 g of methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate. The resulting solutionwas stirred under nitrogen overnight at room temperature, quenched with5N aqueous hydrochloric acid, and extracted with ethyl acetate. Theresidue obtained from evaporation of solvent was washed with ether toafford 0.6 g of product, mp 184°-5°, which showed absorption peaks at1.8-2.2 ppm and 3.2-3.8 ppm for the pyrrolidine ring and no methyl esterpeak, and all other signals indicative of the desired product.

                                      TABLE I-a                                   __________________________________________________________________________     ##STR103##                                                                   A'   R.sup.I      W R.sub.5                                                                          X     Y              m.p. (°C.)                 __________________________________________________________________________    H    CH.sub.3     O H  CH.sub.3                                                                            Cl                                               H    CH.sub.3     O H  H     H                                                H    CH.sub.3     O H  Cl    Cl                                               H    CH.sub.3     O H  OCH.sub.2 CH.sub.3                                                                  CH.sub.2 CH.sub.3                                H    CH.sub.3     O H  CH.sub.3                                                                            CH.sub.2 CH.sub.3                                H    CH.sub.3     O H  CH.sub.3                                                                            CH.sub.3 CH.sub.2 OCH.sub.3                      H    CH.sub.3     O H  CH.sub.3                                                                            (CH.sub.2).sub.4 OCH.sub.3                       H    CH.sub.3     O H  CH.sub.3                                                                            (CH.sub.2).sub.2 OC.sub.2 H.sub.5                H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CN                                      H    CH.sub.3     O H  OCH.sub.3                                                                            ##STR104##                                      H    CH.sub.3     O H  OCH.sub.3                                                                           (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CF.sub.3                                H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                             H    CH.sub.3     O H  OCH.sub.3                                                                           CF.sub.3                                         H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CCl.sub.3                               H    CH.sub.3     O H  OCH.sub.3                                                                           (CH.sub.2).sub.4 Cl                              H    CH.sub.3     O H  OCH.sub.3                                                                           (CH.sub.2).sub.3 Br                              H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CHCH.sub.2                              H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.2 CHCHCH.sub.2                            H    CH.sub.3     O H  CH.sub.3                                                                            O(CH.sub.2).sub.2 OCH.sub.3                      H    CH.sub.3     O H  CH.sub.3                                                                            O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H    CH.sub.3     O H  CH.sub.3                                                                            O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2            H    CH.sub.3     O H  CH.sub.3                                                                            O(CH.sub.2).sub.3 O(CH.sub.2).sub.2 CH.sub.3     H    CH.sub.3     O H  CH.sub.3                                                                             ##STR105##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR106##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR107##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR108##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR109##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR110##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR111##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR112##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR113##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR114##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR115##                                      H    CH.sub.3     O H  CH.sub.3                                                                            SCN                                              H    CH.sub.3     O H  CH.sub.3                                                                            N.sub.3                                          H    CH.sub.3     O H  CH.sub.3                                                                            NH.sub.2                                         H    CH.sub.3     O H  CH.sub.3                                                                            NHCH.sub.3                                       H    CH.sub.3     O H  CH.sub.3                                                                             ##STR116##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR117##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR118##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR119##                                      H    CH.sub.3     O H  CH.sub.3                                                                            NHCH.sub.2 CHCH.sub.2                            H    CH.sub.3     O H  CH.sub.3                                                                            NHCH.sub.2 CHCHCH.sub.2                          H    CH.sub.3     O H  CH.sub.3                                                                             ##STR120##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR121##                                      H    CH.sub.3     O H  CH.sub.3                                                                            NH(CH.sub.2).sub.2 OC.sub.2 H.sub.5              H    CH.sub.3     O H  CH.sub.3                                                                             ##STR122##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR123##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR124##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR125##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR126##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR127##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR128##                                      H    CH.sub.3     O H  CH.sub.3                                                                            OC.sub.2 H.sub.5                                 H    CH.sub.3     O H  CH.sub.3                                                                            O -n-C.sub.3 H                                   H    CH.sub.3     O H  CH.sub.3                                                                            OCH(CH.sub.3).sub.2                              H    CH.sub.3     O H  CH.sub.3                                                                             ##STR129##                                      H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2 CF.sub.3                               H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Cl                            H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2 CH.sub.2 Br                            H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2 CCl.sub.3                              H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2 CN                                     H    CH.sub.3     O H  CH.sub.3                                                                             ##STR130##                                      H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2CHCHCH.sub.3                            H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2CCH                                     H    CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.2CCCH.sub.2 Cl                           H    CH.sub.3     O H  CH.sub.3                                                                             ##STR131##                                      H    CH.sub.3     O H  CH.sub.3                                                                             ##STR132##                                      H    CH.sub.3     O H  CH.sub.3                                                                            SCH.sub.3                                        H    CH.sub.3     O H  CH.sub.3                                                                            SCH(CH.sub.3).sub.2                              H    CH.sub.3     O H  CH.sub.3                                                                            S -n-C.sub.4 H.sub.9                             H    CH.sub.3     O H  CH.sub.3                                                                            SCH.sub.2 CHCH.sub.2                             5-CH.sub.3                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-CH.sub.3                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Cl CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Cl CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Cl CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Br CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Br CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Br CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-C.sub.2 H.sub.5                                                                  CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-n-C.sub.4 H.sub.9                                                                CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.5 CN                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CHCHCH.sub.2 Cl                                                                   O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CHCH(CH.sub.2).sub.2 Cl                                                           O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CCCH.sub.2 Cl                                                                     O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CC(CH.sub.2).sub.3 Cl                                                             O H  CH.sub.3                                                                            OCH.sub.3                                              ##STR133##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR134##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR135##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR136##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR137##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR138##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR139##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR140##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR141##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR142##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR143##  O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.3     O H  OCH.sub.3                                                                           SCH.sub.2CCH                                     H    CH.sub.3     O H  OCH.sub.3                                                                            ##STR144##                                      H    CH.sub.3     O H  OCH.sub.3                                                                           SCH.sub.2 CN                                     H    CH.sub.3     S H  OCH.sub.3                                                                           CH.sub.3                                         H    CH.sub.3     S H  CH.sub.3                                                                            CH.sub.3                                         H    CH.sub.3     S H  OCH.sub.3                                                                           CH.sub.3                                         H    CH.sub.3     S H  OCH.sub.3                                                                           CH.sub.3                                         H    CH.sub.3     S CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.3     S CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.3     S H  OCH.sub.3                                                                           OC.sub.2 H.sub.5                                 H    CH.sub.3     O CH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.3     O CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.3     O CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3                                         H    CH.sub.3     O CH.sub.3                                                                         CH.sub.3                                                                            OCH.sub.2 CO.sub.2 CH.sub.3                      4-Cl CH.sub. 3    O H  CH.sub.3                                                                            OCH.sub.3                                        4-Cl CH(CH.sub.3).sub.2                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        4-Cl CH.sub.2 CHCH.sub.2                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        4-Br C.sub.2 H.sub.5                                                                            O H  CH.sub.3                                                                            OCH.sub.3                                        4-CH.sub.3                                                                         CH.sub.2 CH.sub.2 Cl                                                                       O H  CH.sub.3                                                                            OCH.sub.3                                        4-C.sub.2 H.sub.5                                                                  CH(CH.sub.3).sub.2                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        4- -n-C.sub.4 H.sub.9                                                              CH.sub.2 CHCH.sub.2                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        4- .sub.-i-C.sub.3 H.sub.7                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-Cl C.sub.2 H.sub.5                                                                            O H  CH.sub.3                                                                            OCH.sub.3                                        5-Br CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-CH.sub.3                                                                         CH(CH.sub.3).sub.2                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    C.sub.2 H.sub.5                                                                            O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CHCH.sub.2                                                                        O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.3 CH.sub.3                                                                  O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.4 CH.sub.3                                                                  O H  OCH.sub.3                                                                           OCH.sub.3                                        H                                                                                   ##STR145##  O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.5 CH.sub.3                                                                  O H  OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.2 CHCHCH.sub.3                                                                      O H  OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.2 CHCHC.sub.2 H.sub.5                                                               O H  OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.2 CHCHCH(CH.sub.3).sub.2                                                            O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.3 Cl                                                                        O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.5 Cl                                                                        O H  OCH.sub.3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.6 OCH.sub.3                                                                 O H  OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.2 CN  O H  OCH.sub.3                                                                           OCH.sub.3                                        4-OCH.sub.3                                                                        CH.sub.3     O H  CH.sub.3                                                                            CH.sub.3                                         5-OCH.sub.3                                                                        CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        4-NO.sub.2                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-NO.sub.2                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        4-CF.sub.3                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        5-CF.sub.3                                                                         CH.sub.3     O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                              O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CCl.sub.3                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.6 Cl                                                                        O H  CH.sub. 3                                                                           OCH.sub.3                                        H    (CH.sub.2).sub.4 Cl                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CBr.sub.3                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.4 Br                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.6 Br                                                                        O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.6 F                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.4 F                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    (CH.sub.2).sub.3 F                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CF.sub.3                                                                          O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 CN  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR146##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR147##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR148##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR149##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR150##  O H  CH.sub. 3                                                                           OCH.sub.3                                        H                                                                                   ##STR151##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR152##  O H  CH.sub.3                                                                            OCH.sub.3                                        H                                                                                   ##STR153##  O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 OCH.sub.3                                                                         O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 OC.sub.2 H.sub.5                                                                  O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 OCH(CH.sub.3).sub.2                                                               O H  CH.sub.3                                                                            OCH.sub.3                                        H    CH.sub.2 O -n-C.sub.4 H.sub.9                                                              O H  CH.sub.3                                                                            OCH.sub.3                                        H    H            O H  CH.sub.3                                                                            CH.sub.3                                         H    H            O H  CH.sub.3                                                                            OCH.sub.3                                        H    H            O H  OCH.sub.3                                                                           OCH.sub.3                                        H    CH.sub.3     O H  CH.sub.3                                                                            CH.sub.3       191-193                           H    CH.sub.3     O H  OCH.sub.3                                                                           OCH.sub.3      191-193                           H    CH.sub.3     O H  OCH.sub.3                                                                           CH.sub.3       165-173                           H    CH.sub.2 C.sub.6 H.sub.5                                                                   O H  CH.sub.3                                                                            CH.sub.3       133-136                           H    CH(CH.sub.3 ).sub.2                                                                        O H  OCH.sub.3                                                                           OCH.sub.3      155-160                           H    CH.sub.2 CHCH.sub.2                                                                        O H  CH.sub.3                                                                            OCH.sub.3      164-165                           H    CH(CH.sub.3).sub.2                                                                         O H  CH.sub.3                                                                            OCH.sub.3      153-161                           H    CH(CH.sub.3)C.sub.2 H.sub.5                                                                O H  CH.sub.3                                                                            OCH.sub.3      146-156                           H    CH(CH.sub.3)CHCH.sub.2                                                                     O H  CH.sub.3                                                                            OCH.sub.3      152-154                           H    CH(CH.sub.3)CCH                                                                            O H  CH.sub.3                                                                            OCH.sub.3      167-173                           H    CH.sub.3     O H  CH.sub.3                                                                            CF.sub.3       171-175                           H    CH.sub.3     O H  CH.sub.3                                                                            SCH.sub.3      128-142                           H    CH.sub.3     O H  CH.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                           183-187                           H    CH.sub.3     O H  CH.sub.3                                                                            Cl             155-158                           H    CH.sub.3     O H  CH.sub.3                                                                            N(CH.sub.3).sub.2                                                                            225-228                           H    CH.sub.3     O H  Cl    N(CH.sub.3).sub.2                                                                            205-207                           H    CH.sub.3     O H  CH.sub.3                                                                            CH.sub.3       198-199                           H    CH.sub.2 CHCH.sub.2                                                                        O H  CH.sub.3                                                                            CH.sub.3       173-175 (d)                       H    CH.sub.2 CHCH.sub.2                                                                        O H  OCH.sub.3                                                                           OCH.sub.3      140-145 (d)                       H    CH.sub.3     O H  CH.sub.3                                                                            H              184-185 (d)                       H    CH.sub.3     O H  CH.sub.3                                                                            C.sub.2 H.sub.5                                                                              160-169                           H    CH.sub.3     O H  CH.sub.3                                                                            CH(CH.sub.3).sub.2                                                                           130-139                           H    CH(CH.sub.3)CCH                                                                            O H  CH.sub.3                                                                            CH.sub.3       --                                H    CH.sub.3     O H  CH.sub.3                                                                            N(CH.sub.3)OCH.sub.3                                                                         150-154 (d)                       __________________________________________________________________________

                  TABLE I-b                                                       ______________________________________                                         ##STR154##                                                                   A'  R.sup.I                                                                              W     R.sub.5                                                                           X       Y           m.p. (°C.)                    ______________________________________                                        H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                               H   CH.sub.3                                                                             O     H   H       H                                                H   CH.sub.3                                                                             O     H   Cl      Cl                                               H   CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                       H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR155##                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                         H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2             H  CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3    179-181(d)                           H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.3    149-159(d)                           H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3   189-190(d)                           ______________________________________                                    

                  TABLE I-c                                                       ______________________________________                                         ##STR156##                                                                   A'    R.sup.I                                                                              W     R.sub.5                                                                           X       Y         m.p. (°C.)                    ______________________________________                                        H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                             H     CH.sub.3                                                                             O     H   H       H                                              H     CH.sub.3                                                                             O     H   Cl      Cl                                             H     CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                              H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                             H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                              H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                    H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                     H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5              H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                    H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR157##                                    H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3             H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5              H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                              H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                           H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                       H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                             H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                            H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                            H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                            H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                          H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                    H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5             H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2          H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              OCH.sub.3 182-183.5                            H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3  169-172(d)                           H     CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3 179-181                              H     CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                      154-157(d)                           5-C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3  180-185                              5-C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             O     H   CH.sub.3                                                                              OCH.sub.3 150-154(d)                           5-C.sub.2 H.sub.5                                                                   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3 158-161                              ______________________________________                                    

                                      TABLE I-d                                   __________________________________________________________________________     ##STR158##                                                                   A'                                                                              R.sup.I W R.sub.5                                                                           X     Y          m.p. (°C.)                            __________________________________________________________________________    H CH.sub.3                                                                              O H   CH.sub.3                                                                            Cl                                                      H CH.sub.3                                                                              O H   H     H                                                       H CH.sub.3                                                                              O H   Cl    Cl                                                      H CH.sub.3                                                                              O H   OCH.sub.2 CH.sub.3                                                                  CH.sub.2 CH.sub.3                                       H CH.sub.3                                                                              O H   CH.sub.3                                                                            CH(CH.sub.3).sub.2                                      H CH.sub.3                                                                              O H   CH.sub.3                                                                            CH.sub.2 CH.sub.3                                       H CH.sub.3                                                                              O H   CH.sub.3                                                                            CH.sub.2 OCH.sub.3                                      H CH.sub.3                                                                              O H   CH.sub.3                                                                            CH.sub.3 CH.sub.2 OCH.sub.3                             H CH.sub.3                                                                              O H   CH.sub.3                                                                            (CH.sub.2).sub.4 OCH.sub.3                              H CH.sub.3                                                                              O H   CH.sub. 3                                                                           (CH.sub.2).sub.2 OC.sub.2 H.sub.5                       H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CN                                             H CH.sub.3                                                                              O H   OCH.sub.3                                                                            ##STR159##                                             H CH.sub.3                                                                              O H   OCH.sub.3                                                                           (CH.sub.2).sub.3 CO.sub.2 CH.sub.3                      H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                       H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CF.sub.3                                       H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                                    H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CF.sub.3                                                H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CCl.sub.3                                      H CH.sub.3                                                                              O H   OCH.sub.3                                                                           (CH.sub.2).sub.4 Cl                                     H CH.sub.3                                                                              O H   OCH.sub.3                                                                           (CH.sub.2).sub.3 Br                                     H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CHCH.sub.2                                     H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 CHCHCH.sub.2                                   H CH.sub.3                                                                              O H   CH.sub.3                                                                            O(CH.sub.2).sub.2 OCH.sub.3                             H CH.sub.3                                                                              O H   CH.sub.3                                                                            O(CH.sub.2).sub.3 OC.sub.2 H.sub.5                      H CH.sub.3                                                                              O H   CH.sub.3                                                                            O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2                   H CH.sub.3                                                                              O H   CH.sub.3                                                                            CH.sub.3   158-171                                      H CH.sub.3                                                                              O H   OCH.sub.3                                                                           OCH.sub.3  181-183                                      H CH.sub.3                                                                              O H   CH.sub.3                                                                            OCH.sub.3  166-170                                      H CH(CH.sub.3).sub.2                                                                    O H   CH.sub.3                                                                            CH.sub.3   195-196(d)                                   H CH(CH.sub.3).sub.2                                                                    O H   CH.sub.3                                                                            OCH.sub.3  179-181(d)                                   H CH(CH.sub.3).sub.2                                                                    O H   OCH.sub.3                                                                           OCH.sub.3  178-180(d)                                   H CH.sub.2 CHCH.sub.2                                                                   O H   CH.sub.3                                                                            OCH.sub.3  142-146(d)                                   H CH.sub.2 CHCH.sub.2                                                                   O H   OCH.sub.3                                                                           OCH.sub.3  151-155(d)                                   H CH.sub.3                                                                              O H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        173-175                                      H CH.sub.3                                                                              O H   OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                       179-181                                      H CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3  185-187                                      H CH.sub.3                                                                              O CH.sub.3                                                                          CH.sub.3                                                                            Cl         134-138                                      H CH.sub.3                                                                              O CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3   139-145                                      H CH.sub.3                                                                              O OCH.sub.3                                                                         OCH.sub.3                                                                           OCH.sub.3  175-177                                      __________________________________________________________________________

                  TABLE I-e                                                       ______________________________________                                         ##STR160##                                                                   A'  R.sup.I   W     R.sub.5                                                                           X       Y        m.p. (°C.)                    ______________________________________                                        H   CH.sub.3  O     H   CH.sub.3                                                                              Cl                                            H   CH.sub.3  O     H   H       H                                             H   CH.sub.3  O     H   Cl      Cl                                            H   CH.sub.3  O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                             H   CH.sub.3  O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                            H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                             H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                            H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                   H   CH.sub.3  O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                    H   CH.sub.3  O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CN                                   H   CH.sub.3  O     H   OCH.sub.3                                                                              ##STR161##                                   H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3            H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                          H   CH.sub.3  O     H   OCH.sub.3                                                                             CF.sub.3                                      H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                            H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                           H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                           H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                           H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                         H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                   H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5            H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2         H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.3 184-187(d)                           H   CH.sub.3  O     H   CH.sub.3                                                                              OCH.sub.3                                                                              196-198(d)                           H   CH.sub.3  O     H   OCH.sub.3                                                                             OCH.sub.3                                                                              192-195                              H   CH(CH.sub.3).sub.2                                                                      O     H   CH.sub.3                                                                              CH.sub.3 155-157                              H   CH(CH.sub.3).sub.2                                                                      O     H   CH.sub.3                                                                              OCH.sub.3                                                                              166-170                              H   CH(CH.sub.3).sub.2                                                                      O     H   OCH.sub.3                                                                             OCH.sub.3                                                                              176-177                              ______________________________________                                    

                  TABLE I-f                                                       ______________________________________                                         ##STR162##                                                                   A'  R.sup.I   W     R.sub.5                                                                           X       Y        m.p. (°C.)                    ______________________________________                                        H   CH.sub.3  O     H   CH.sub.3                                                                              Cl                                            H   CH.sub.3  O     H   H       H                                             H   CH.sub.3  O     H   Cl      Cl                                            H   CH.sub.3  O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                             H   CH.sub.3  O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                            H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                             H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                            H   CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                   H   CH.sub.3  O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                    H   CH.sub.3  O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CN                                   H   CH.sub.3  O     H   OCH.sub.3                                                                              ##STR163##                                   H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3            H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                             H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                          H   CH.sub.3  O     H   OCH.sub.3                                                                             CF.sub.3                                      H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                            H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                           H   CH.sub.3  O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                           H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                           H   CH.sub.3  O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                         H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                   H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5            H   CH.sub.3  O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2          H  CH.sub.3  O     H   CH.sub.3                                                                              CH.sub.3 165-175                              H   CH.sub.3  O     H   CH.sub.3                                                                              OCH.sub.3                                                                              170-72(d)                            H   CH.sub.3  O     H   OCH.sub.3                                                                             OCH.sub.3                                                                              --                                   H   CH(CH.sub.3).sub.2                                                                      O     H   CH.sub.3                                                                              CH.sub.3 158-160                              H   CH(CH.sub.3).sub.2                                                                      O     H   CH.sub.3                                                                              OCH.sub.3                                                                              106-111                              H   CH(CH.sub.3).sub.2                                                                      O     H   OCH.sub.3                                                                             OCH.sub.3                                                                              165-167                              ______________________________________                                    

                  TABLE I-g                                                       ______________________________________                                         ##STR164##                                                                   A'  R.sup.I                                                                              W     R.sub.5                                                                           X       Y           m.p. (°C.)                    ______________________________________                                        H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                               H   CH.sub.3                                                                             O     H   H       H                                                H   CH.sub.3                                                                             O     H   Cl      Cl                                               H   CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                       H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub. 5               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR165##                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                         H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2            H   CH.sub.3                                                                             O      H  CH.sub.3                                                                              CH.sub.3    194-196                              H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              OCH.sub.3   162-165                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3   205-207                              ______________________________________                                    

                  TABLE I-h                                                       ______________________________________                                         ##STR166##                                                                   A'  R.sup.I                                                                              W     R.sub.5                                                                           X       Y           m.p. (°C.)                    ______________________________________                                        H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                               H   CH.sub.3                                                                             O     H   H       H                                                H   CH.sub.3                                                                             O     H   Cl      Cl                                               H   CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                       H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub. 2).sub.2 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR167##                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                         H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2            H    CH.sub.3                                                                            O     H   OCH.sub.3                                                                             CH.sub.3    168-170                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3   164-167                              ______________________________________                                    

                  TABLE I-i                                                       ______________________________________                                         ##STR168##                                                                   A'  R.sup.I                                                                              W     R.sub.5                                                                           X       Y           m.p. (°C.)                    ______________________________________                                        H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                               H   CH.sub.3                                                                             O     H   H       H                                                H   CH.sub.3                                                                             O     H   Cl      Cl                                               H   CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                       H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub. 5               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR169##                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                         H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2            H   CH.sub.3                                                                             O      H  CH.sub.3                                                                              CH.sub.3    189-190                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.3    189-190                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3   180-182                              ______________________________________                                    

                  TABLE I-j                                                       ______________________________________                                         ##STR170##                                                                   A'  R.sup.I                                                                              W     R.sub.5                                                                           X       Y            m.p.(°C.)                    ______________________________________                                        H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              Cl                                               H   CH.sub.3                                                                             O     H   H       H                                                H   CH.sub.3                                                                             O     H   Cl      Cl                                               H   CH.sub.3                                                                             O     H   OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH(CH.sub.3).sub.2                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 CH.sub.3                                H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                       H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CN                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                              ##STR171##                                      H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CF.sub.3                                         H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                               H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                              H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                      H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5               H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.2            H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              OCH.sub.3    160-163                             H   CH.sub.3                                                                             O     H   OCH.sub.3                                                                             OCH.sub.3    173-175                             H   CH.sub.3                                                                             O     H   CH.sub.3                                                                              CH.sub.3     174-176                             ______________________________________                                    

                  TABLE I-k                                                       ______________________________________                                         ##STR172##                                                                                                               m.p.                              A'  R.sup.I W     R.sub.5                                                                            X       Y            (°C.)                      ______________________________________                                        H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              Cl                                             H   CH.sub.3                                                                              O     H    H       H                                              H   CH.sub.3                                                                              O     H    Cl      Cl                                             H   CH.sub.3                                                                              O     H    OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH(CH.sub.3).sub.2                             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.2 OCH.sub.3                             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                    H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                     H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CN                                    H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                              ##STR173##                                    H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3             H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                           H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CF.sub.3                                       H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                             H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                          H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                    H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3                 ______________________________________                                                                       ).sub.2                                    

                  TABLE I-1                                                       ______________________________________                                         ##STR174##                                                                                                               m.p.                              A'  R.sup.I W     R.sub.5                                                                            X       Y            (°C.)                      ______________________________________                                        H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              Cl                                             H   CH.sub.3                                                                              O     H    H       H                                              H   CH.sub.3                                                                              O     H    Cl      Cl                                             H   CH.sub.3                                                                              O     H    OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH(CH.sub.3).sub.2                             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.2 OCH.sub.3                             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              CH.sub.3 CH.sub.2 OCH.sub.3                    H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              (CH.sub.2).sub.4 OCH.sub.3                     H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              (CH.sub.2).sub.2 OC.sub.2 H.sub.5              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CN                                    H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                              ##STR175##                                    H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.3 CO.sub.2 CH.sub.3             H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CH.sub.3                              H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CH.sub.2 Cl                           H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CF.sub.3                                       H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CCl.sub.3                             H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.4 Cl                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             (CH.sub.2).sub.3 Br                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CHCH.sub.2                            H   CH.sub.3                                                                              O     H    OCH.sub.3                                                                             CH.sub.2 CHCHCH.sub.2                          H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH.sub.3                    H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.3 OC.sub.2 H.sub.5             H   CH.sub.3                                                                              O     H    CH.sub.3                                                                              O(CH.sub.2).sub.2 OCH(CH.sub.3).sub.           ______________________________________                                                                       2                                          

                  TABLE II-a                                                      ______________________________________                                         ##STR176##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    CH.sub. 3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-b                                                      ______________________________________                                         ##STR177##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-c                                                      ______________________________________                                         ##STR178##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                                                            129° (d)                      H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-d                                                      ______________________________________                                         ##STR179##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                                                           126-133°                      5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-e                                                      ______________________________________                                         ##STR180##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    0     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-f                                                      ______________________________________                                         ##STR181##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-g                                                      ______________________________________                                         ##STR182##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-h                                                      ______________________________________                                         ##STR183##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    CH.sub. 3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-i                                                      ______________________________________                                         ##STR184##                                                                   A'    R.sup.1     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-j                                                      ______________________________________                                         ##STR185##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-k                                                      ______________________________________                                         ##STR186##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    CH.sub. 3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE II-l                                                      ______________________________________                                         ##STR187##                                                                   A'    R.sup.I     W     R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3    O     H    H     H                                          H     CH.sub.3    O     H    H     OCH.sub.3                                  H     CH.sub.3    O     H    H     CH.sub.3                                   H     CH.sub.3    O     H    Cl    H                                          H     CH.sub.3    O     H    Cl    OCH.sub.3                                  H     CH.sub.3    O     H    Cl    CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           H                                          H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     H    OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    H                                          H     CH.sub.3    O     H    OC.sub.2 H.sub.5                                                                    OCH.sub.3                                  H     CH.sub.3    O     H    OC.sub.2 H.sub. 5                                                                   CH.sub.3                                   H     CH.sub.3    O     H    CH.sub.3                                                                            H                                          H     CH.sub.3    O     H    CH.sub.3                                                                            OCH.sub.3                                  H     CH.sub.3    O     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Cl  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-Br  CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  5-C.sub.2 H.sub.5                                                                   CH.sub.3    O     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH(CH.sub.3).sub.2                                                                        O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.2 CHCH.sub.2                                                                       O     CH   OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    O     CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                   H     CH.sub.3    S     H    CH.sub.3                                                                            CH.sub.3                                   H     CH.sub.3    S     H    OCH.sub.3                                                                           OCH.sub.3                                  H     CH.sub.3    S     H    H     H                                          H     CH(CH.sub.3).sub.2                                                                        S     H    CH.sub.3                                                                            CH.sub.3                                   ______________________________________                                    

                  TABLE III-a                                                     ______________________________________                                         ##STR188##                                                                   A'    R.sup.I   W      R.sub.5                                                                             X.sub.11                                                                            Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3  O      H     CH.sub.2                                                                            H                                          H     CH.sub.3  O      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  O      H     CH.sub.2                                                                            CH.sub.3                                   H     CH.sub.3  O      H     O     H                                          H     CH.sub.3  O      H     O     OCH.sub.3                                  H     CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   H     CH.sub.3  S      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH.sub. 3 S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      H     O     CH.sub.3                                   H     CH.sub.3  O      CH.sub.3                                                                            O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                            O     CH.sub.3                                   ______________________________________                                    

                  TABLE III-b                                                     ______________________________________                                         ##STR189##                                                                   A'    R.sup.I   W      R.sub.5                                                                             X.sub.11                                                                            Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3  O      H     CH.sub.2                                                                            H                                          H     CH.sub.3  O      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  O      H     CH.sub.2                                                                            CH.sub.3                                   H     CH.sub.3  O      H     O     H                                          H     CH.sub.3  O      H     O     OCH.sub.3                                  H     CH.sub.3  O      H     O     CH.sub.3                                                                            147-155(d)                           5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   H     CH.sub.3  S      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      H     O     CH.sub.3                                   H     CH.sub.3  O      CH.sub.3                                                                            O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                            O     CH.sub.3                                   ______________________________________                                    

                  TABLE III-c                                                     ______________________________________                                         ##STR190##                                                                   A'    R.sup.I   W      R.sub.5                                                                             X.sub.11                                                                            Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3  O      H     CH.sub.2                                                                            H                                          H     CH.sub.3  O      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  O      H     CH.sub.2                                                                            CH.sub.3                                   H     CH.sub.3  O      H     O     H                                          H     CH.sub.3  O      H     O     OCH.sub.3                                  H     CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   H     CH.sub.3  S      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      H     O     CH.sub.3                                   H     CH.sub.3  O      CH.sub.3                                                                            O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                            O     CH.sub.3                                   ______________________________________                                    

                  TABLE III-d                                                     ______________________________________                                         ##STR191##                                                                   A'    R.sup.I   W      R.sub.5                                                                             X.sub.11                                                                            Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H     CH.sub.3  O      H     CH.sub.2                                                                            H                                          H     CH.sub.3  O      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  O      H     CH.sub.2                                                                            CH.sub.3                                   H     CH.sub.3  O      H     O     H                                          H     CH.sub.3  O      H     O     OCH.sub.3                                  H     CH.sub.3  O      H     O     CH.sub.3                                                                            180-182°                      5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-CH.sub.3                                                                          CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   5-Cl  CH.sub.3  O      H     O     CH.sub.3                                   H     CH.sub.3  S      H     CH.sub.2                                                                            OCH.sub.3                                  H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH.sub.3  S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      S      H     O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      H     O     CH.sub.3                                   H     CH.sub.3  O      CH.sub.3                                                                            O     CH.sub.3                                   H     CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                            O     CH.sub.3                                   ______________________________________                                    

                  TABLE III-e                                                     ______________________________________                                         ##STR192##                                                                   A'     R.sup.I   W      R.sub.5                                                                            X.sub.11                                                                           Y.sub.1                                                                             m.p. (°C.)                     ______________________________________                                        H      CH.sub.3  O      H    CH.sub.2                                                                           H                                           H      CH.sub.3  O      H    CH.sub.2                                                                           OCH.sub.3                                   H      CH.sub.3  O      H    CH.sub.2                                                                           CH.sub.3                                    H      CH.sub.3  O      H    O    H                                           H      CH.sub.3  O      H    O    OCH.sub.3                                   H      CH.sub.3  O      H    O    CH.sub.3                                                                            175° (d)                       5-CH.sub.3                                                                           CH.sub.3  O      H    O    CH.sub.3                                    5-CH.sub.3                                                                           CH.sub.3  O      H    O    CH.sub.3                                    5-Cl   CH.sub.3  O      H    O    CH.sub.3                                    5-Cl   CH.sub.3  O      H    O    CH.sub.3                                    H      CH.sub.3  S      H    CH.sub.2                                                                           OCH.sub.3                                   H      CH.sub.3  S      H    O    CH.sub.3                                    H      CH.sub.3  S      H    O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      S      H    O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      O      H    O    CH.sub.3                                    H      CH.sub.3  O      CH.sub.3                                                                           O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                           O    CH.sub.3                                    ______________________________________                                    

                  TABLE III-f                                                     ______________________________________                                         ##STR193##                                                                   A'     R.sup.I   W      R.sub.5                                                                            X.sub.11                                                                           Y.sub.1                                                                             m.p. (°C.)                     ______________________________________                                        H      CH.sub.3  O      H    CH.sub.2                                                                           H                                           H      CH.sub.3  O      H    CH.sub.2                                                                           OCH.sub.3                                   H      CH.sub.3  O      H    CH.sub.2                                                                           CH.sub.3                                    H      CH.sub.3  O      H    O    H                                           H      CH.sub.3  O      H    O    OCH.sub.3                                   H      CH.sub.3  O      H    O    CH.sub.3                                    5-CH.sub.3                                                                           CH.sub.3  O      H    O    CH.sub.3                                    5-CH.sub.3                                                                           CH.sub.3  O      H    O    CH.sub.3                                    5-Cl   CH.sub.3  O      H    O    CH.sub.3                                    5-Cl   CH.sub.3  O      H    O    CH.sub.3                                    H      CH.sub.3  S      H    CH.sub.2                                                                           OCH.sub.3                                   H      CH.sub.3  S      H    O    CH.sub.3                                    H      CH.sub.3  S      H    O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      S      H    O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      O      H    O    CH.sub.3                                    H      CH.sub.3  O      CH.sub.3                                                                           O    CH.sub.3                                    H      CH(CH.sub.3).sub.2                                                                      O      CH.sub.3                                                                           O    CH.sub.3                                    ______________________________________                                    

                  TABLE IV-a                                                      ______________________________________                                         ##STR194##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    0      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE IV-b                                                      ______________________________________                                         ##STR195##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE IV-c                                                      ______________________________________                                         ##STR196##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE IV-d                                                      ______________________________________                                         ##STR197##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE IV-e                                                      ______________________________________                                         ##STR198##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub. 3                                5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE IV-f                                                      ______________________________________                                         ##STR199##                                                                                                               m.p.                              A'    R.sup.I     W      R.sub.5                                                                            X     Y       (°C.)                      ______________________________________                                        H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                        H     CH.sub.3    O      H    OC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                           H     CH.sub.3    S      H    OCH.sub.3                                                                           CH.sub.3                                  H     CH.sub.3    S      H    CH.sub.3                                                                            CH.sub.3                                  H     CH.sub.3    O      CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                 H     CH.sub.3    O      CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 5-Cl  CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 5-CH.sub.3                                                                          CH.sub.3    O      H    CH.sub.3                                                                            CH.sub.3                                  5-CH.sub.3                                                                          CH.sub.3    O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     C.sub.2 H.sub.5                                                                           O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH(CH.sub.3).sub.2                                                                        O      H    OCH.sub.3                                                                           OCH.sub.3                                 H     CH.sub.2 CHCH.sub.2                                                                       O      H    OCH.sub.3                                                                           OCH.sub.3                                 ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR200##                                                                   A'   R.sup.I   R.sub.5                                                                              X     Y      Z     m.p. (°C.)                    ______________________________________                                        H    CH.sub.3  H      CH.sub.3                                                                            CH.sub.3                                                                             CH                                         H    CH.sub.3  H      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                         H    CH.sub.3  H      CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     CH                                         H    CH.sub.3  H      OCH.sub.3                                                                           OCH.sub.3                                                                            CH                                         H    CH(CH.sub.3).sub.2                                                                      H      OCH.sub.3                                                                           CH.sub.3                                                                             N                                          H    CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                          H    CH.sub.3  H      CH.sub.3                                                                            CH.sub.3                                                                             N                                          H    CH.sub.3  H      CH.sub.3                                                                            CH.sub.3                                                                             CCH.sub.3                                  H    CH.sub.3  H      CH.sub.3                                                                            OCH.sub.3                                                                            CCH.sub.3                                  ______________________________________                                    

                  TABLE VI                                                        ______________________________________                                         ##STR201##                                                                                                               m.p.                              A'   R.sup.I                                                                              WR.sup.IV     X     Y     Z     (°C.)                      ______________________________________                                        H    CH.sub.3                                                                             OCH.sub.3     CH.sub.3                                                                            CH.sub.3                                                                            N                                       H    CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           CH.sub.3                                                                            N                                       H    CH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                                                                        OCH.sub.3                                                                           CH.sub.3                                                                            N                                       H    CH.sub.3                                                                             OCH.sub.3     OCH.sub.3                                                                           CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             OCH.sub.3     CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             OCH(CH.sub.3).sub.2                                                                         CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             OCH.sub.3     CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             O(CH.sub.2).sub.3 CH.sub.3                                                                  CH.sub.3                                                                            CH.sub. 3                                                                           CH                                      H    CH.sub.3                                                                             OCH.sub.2 CHCHCH.sub.3                                                                      CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CCH.sub.3                               H    CH.sub.3                                                                             SCH.sub.3     CH.sub.3                                                                            OCH.sub.3                                                                           N                                       H    CH.sub.3                                                                             SC.sub.2 H.sub.5                                                                            CH.sub.3                                                                            OCH.sub.3                                                                           N                                       H    CH.sub.3                                                                             SCH.sub.2 CHCH.sub.2                                                                        CH.sub.3                                                                            CH.sub.3                                                                            CH                                      H    CH.sub.3                                                                             S(CH.sub.2).sub.4 CH.sub.3                                                                  CH.sub.3                                                                            CH.sub.3                                                                            CH                                      ______________________________________                                    

                                      TABLE VII-a                                 __________________________________________________________________________     ##STR202##                                                                   A'  QR.sup.I       W  R.sub.5                                                                          X   Y   m.p. (°C.)                            __________________________________________________________________________    H   SCH.sub.3      O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH(CH.sub.3).sub.2                                                                          O  H  CH.sub.3                                                                          OCH.sub.3                                             ##STR203##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR204##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CHCH.sub.2                                                                         O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2CCC.sub.2 H.sub.5                                                                   O  H  CH.sub.3                                                                          OCH.sub.3                                        H   S(CH.sub. 2).sub.4 Cl                                                                        O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CN   O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                              S(CH.sub.2).sub.2 OCH.sub.3                                                                  O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                              S(CH.sub.2).sub.4 OCH.sub.3                                                                  O  H  CH.sub.3                                                                          OCH.sub.3                                        5-CH.sub.3                                                                        SCH.sub.2 CHCHCH.sub.2 Cl                                                                    O  H  CH.sub.3                                                                          OCH.sub.3                                        5-C.sub.2 H.sub.5                                                                 SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                             O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR205##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR206##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR207##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR208##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR209##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   NH.sub.2       O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR210##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(CH.sub.2 CN).sub.2                                                                         O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(CH.sub.2 CH.sub.2 CN).sub.2                                                                O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(C.sub.2 H.sub.5).sub.2                                                                     O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR211##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(CH.sub.2 CHCH.sub.2).sub.2                                                                 O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                               ##STR212##    O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                               ##STR213##    O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Br                                                                              NHCH.sub.3     O  H  CH.sub.3                                                                          CH.sub.3                                         5-CH.sub.3                                                                        NHC.sub.2 H.sub.5                                                                            O  H  CH.sub.3                                                                          CH.sub.3                                         5-CH.sub.3                                                                        NHCH(CH.sub.3).sub.2                                                                         O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR214##    O  H  CH.sub.3                                                                          CH.sub.3                                         H   NH(CH.sub.2).sub.5 CH.sub.3                                                                  O  H  CH.sub.3                                                                          CH.sub.3                                         H   NH(CH.sub.2)OCH.sub.3                                                                        O  H  CH.sub.3                                                                          CH.sub.3                                         H   NH(CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                          O  H  CH.sub.3                                                                          CH.sub.3                                         H   NH(CH.sub.2 ).sub.2 OCH(CH.sub.3).sub.2                                                      O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR215##    O  H  CH.sub.3                                                                          CH.sub.3                                         H   NHCH.sub.2 CHCH.sub.2                                                                        O  CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                         H   NHCH.sub.2 CHCHC.sub.2 H.sub.5                                                               O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR216##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR217##    O  CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR218##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR219##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR220##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR221##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR222##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR223##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR224##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR225##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR226##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR227##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                                  ##STR228##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR229##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR230##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR231##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR232##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR233##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR234##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR235##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR236##    O  H  CH.sub.3                                                                          CH.sub.3                                         H                                                                             H   NHOC.sub.2 H.sub.5H  OCH.sub.                                                                O  H  OCH.sub.3                                                                         CH.sub.3                                                                          159-162                                      H   N(CH.sub.3)OCH.sub.3                                                                         O  H  OCH.sub.3                                                                         OCH.sub.3                                                                         177-179(d)                                   H   (CH.sub.3)OCH.sub.3                                                                          O  H  CH.sub.3                                                                          OCH.sub.3                                                                         180-182.5                                    H   NHOCH.sub.3    O  H  CH.sub.3                                                                          CH.sub.3                                                                          172-174                                      3   CH.sub.3                                                                  H   N(CH.sub.3)OCH.sub.3                                                                         O  H  CH.sub.3                                                                          CH.sub.3                                                                          150-154                                      H                                                                                  ##STR238##    O  H  CH.sub.3                                                                          CH.sub.3                                                                          205-205.5                                    H                                                                                  ##STR239##    O  H  CH.sub.3                                                                          CH.sub.3                                                                          167-170                                      H                                                                                  ##STR240##    O  H  CH.sub.3                                                                          CH.sub.3                                         __________________________________________________________________________

                  TABLE VII-b                                                     ______________________________________                                         ##STR241##                                                                                                               m.p.                              A'    QR.sup.I        W      R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3       O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.2                                                                           O      H   CH.sub.3                                                                           OCH.sub.3                                      ##STR242##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR243##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                 O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub.5                                                                    O      H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN    O      H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                   O      H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                   O      H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                     O      H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                              O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR244##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR245##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR246##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR247##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR248##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2        O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR249##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                 O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                      O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR250##     O      H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-c                                                     ______________________________________                                         ##STR251##                                                                                                               m.p.                              A'    QR.sup.I        W      R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3       O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.2                                                                           O      H   CH.sub.3                                                                           OCH.sub.3                                      ##STR252##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR253##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                 O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub. 5                                                                   O      H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN    O      H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                   O      H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                   O      H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                     O      H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                              O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR254##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR255##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR256##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR257##     O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR258##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2        O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR259##     O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                          O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                 O      H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                      O      H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR260##     O      H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                                      TABLE VII-d                                 __________________________________________________________________________     ##STR261##                                                                   A'  QR.sup.I       W  R.sub.5                                                                          X   Y   m.p. (°C.)                            __________________________________________________________________________    H   SCH.sub.3      O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH(CH.sub.3).sub.2                                                                          H  CH.sub.3                                                                         OCH.sub.3                                                 ##STR262##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR263##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CHCH.sub.2                                                                         O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2CCC.sub.2 H.sub.5                                                                   O  H  CH.sub.3                                                                          OCH.sub.3                                        H   S(CH.sub.2).sub.4 Cl                                                                         O  H  CH.sub.3                                                                          OCH.sub.3                                        H   SCH.sub.2 CN   O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                              S(CH.sub.2).sub.2 OCH.sub.3                                                                  O  H  CH.sub.3                                                                          OCH.sub.3                                        5-Cl                                                                              S(CH.sub.2).sub.4 OCH.sub.3                                                                  O  H  CH.sub.3                                                                          OCH.sub.3                                        5-CH.sub.3                                                                        SCH.sub.2 CHCHCH.sub.2 Cl                                                                    O  H  CH.sub.3                                                                          OCH.sub.3                                        5-C.sub.2 H.sub.5                                                                 SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                             O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR264##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR265##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR266##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR267##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR268##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   NH.sub.2       O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR269##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(CH.sub.2 CN).sub.2                                                                         O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(CH.sub.2 CH.sub.2 CN).sub.2                                                                O  H  CH.sub.3                                                                          OCH.sub.3                                        H   N(C.sub.2 H.sub.5).sub.2                                                                     O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR270##    O  H  CH.sub.3                                                                          OCH.sub.3                                        H                                                                                  ##STR271##    O  H  CH.sub.3                                                                          OCH.sub.3                                                                         113-117°                              __________________________________________________________________________

                  TABLE VII-e                                                     ______________________________________                                         ##STR272##                                                                                                               m.p.                              A'    QR.sup.I           W     R.sub.5                                                                           X    Y   (°C.)                      ______________________________________                                        H     SCH.sub.3          O     H   CH.sub.3                                                                           OCH.sub.3                             H     SCH(CH.sub.3).sub.2                                                                              H     CH.sub.3                                                                          OCH.sub.3                                         ##STR273##        O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR274##        O     H   CH.sub.3                                                                           OCH.sub.3                             H     SCH.sub.2 CHCH.sub.2                                                                             O     H   CH.sub.3                                                                           OCH.sub.3                             H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                             H     SCH.sub.2CCC.sub. 2 H.sub.5                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                             H     S(CH.sub.2).sub.4 Cl                                                                             O     H   CH.sub.3                                                                           OCH.sub.3                             H     SCH.sub.2 CN       O     H   CH.sub.3                                                                           OCH.sub.3                             5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                             5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                             5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                        O     H   CH.sub.3                                                                           OCH.sub.3                             5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                                 O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR275##        O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR276##        O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR277##        O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR278##        O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR279##        O     H   CH.sub.3                                                                           OCH.sub.3                             H     NH.sub.2           O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR280##        O     H   CH.sub.3                                                                           OCH.sub.3                             H     N(CH.sub.2 CN).sub.2                                                                             O     H   CH.sub.3                                                                           OCH.sub.3                             H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                             H     N(C.sub.2 H.sub.5).sub.2                                                                         O     H   CH.sub.3                                                                           OCH.sub.3                             H                                                                                    ##STR281##        O     H   CH.sub.3                                                                           OCH.sub.3                             ______________________________________                                    

                  TABLE VII-f                                                     ______________________________________                                         ##STR282##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR283##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR284##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub.5                                                                     O     H   CH.sub.3                                                                           OCH.sub. 3                              H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR285##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR286##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR287##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR288##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR289##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR290##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR291##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-g                                                     ______________________________________                                         ##STR292##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR293##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR294##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub.5                                                                     O     H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR295##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR296##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR297##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR298##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR299##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR300##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR301##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-h                                                     ______________________________________                                         ##STR302##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR303##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR304##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub.5                                                                     O     H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR305##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR306##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR307##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR308##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR309##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR310##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCHJ.sub.3                              H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR311##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-i                                                     ______________________________________                                         ##STR312##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR313##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR314##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub. 5                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR315##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR316##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR317##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR318##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR319##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR320##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR321##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-j                                                     ______________________________________                                         ##STR322##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR323##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR324##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub. 5                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR325##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR326##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR327##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR328##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR329##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR330##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR331##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE VII-k                                                     ______________________________________                                         ##STR332##                                                                                                               m.p.                              A'    QR.sup.I         W     R.sub.5                                                                           X    Y     (°C.)                      ______________________________________                                        H     SCH.sub.3        O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH(CH.sub.3).sub.3                                                                            O     H   CH.sub.3                                                                           OCH.sub.3                                      ##STR333##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR334##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCH.sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CHCHC.sub.2 H.sub.5                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2CCC.sub.2 H.sub.5                                                                     O     H   CH.sub.3                                                                           OCH.sub. 3                              H     S(CH.sub.2).sub.4 Cl                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     SCH.sub.2 CN     O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.2 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-Cl  S(CH.sub.2).sub.4 OCH.sub.3                                                                    O     H   CH.sub.3                                                                           OCH.sub.3                               5-CH.sub.3                                                                          SCH.sub.2 CHCHCH.sub.2 Cl                                                                      O     H   CH.sub.3                                                                           OCH.sub.3                               5-C.sub.2 H.sub.5                                                                   SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                               O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR335##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR336##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR337##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR338##      O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR339##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     NH.sub.2         O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR340##      O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CN).sub.2                                                                           O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(CH.sub.2 CH.sub.2 CN).sub.2                                                                  O     H   CH.sub.3                                                                           OCH.sub.3                               H     N(C.sub.2 H.sub.5).sub.2                                                                       O     H   CH.sub.3                                                                           OCH.sub.3                               H                                                                                    ##STR341##      O     H   CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                                      TABLE VII-1                                 __________________________________________________________________________     ##STR342##                                                                   A'   QR.sup.I      W  R.sub.5                                                                         X   Y   m.p. (°C.)                             __________________________________________________________________________    H    SCH.sub.3     O  H CH.sub.3                                                                          OCH.sub.3                                         H    SCH(CH.sub.3).sub.2                                                                         O  H CH.sub.3                                                                          OCH.sub.3                                               ##STR343##   O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR344##   O  H CH.sub.3                                                                          OCH.sub.3                                         H    SCH.sub.2 CHCH.sub.2                                                                        O  H CH.sub.3                                                                          OCH.sub.3                                         H    SCH.sub.2 CHCHC.sub.2 H.sub.5                                                               O  H CH.sub.3                                                                          OCH.sub.3                                         H    SCH.sub.2CCC.sub.2 H.sub.5                                                                  O  H CH.sub.3                                                                          OCH.sub.3                                         H    S(CH.sub.2).sub. 2 Cl                                                                       O  H CH.sub.3                                                                          OCH.sub.3                                         H    SCH.sub.2 CN  O  H CH.sub.3                                                                          OCH.sub.3                                         5-Cl S(CH.sub.2).sub.2 OCH.sub.3                                                                 O  H CH.sub.3                                                                          OCH.sub.3                                         5-Cl S(CH.sub.2).sub.4 OCH.sub.3                                                                 O  H CH.sub.3                                                                          OCH.sub.3                                         5-CH.sub.3                                                                         SCH.sub.2 CHCHCH.sub.2 Cl                                                                   O  H CH.sub.3                                                                          OCH.sub.3                                         5-C.sub.2 H.sub.5                                                                  SCH.sub.2 CCCH.sub.2 CH.sub.2 Cl                                                            O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR345##   O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR346##   O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR347##   O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR348##   O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR349##   O  H CH.sub.3                                                                          OCH.sub.3                                         H    NH.sub.2      O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR350##   O  H CH.sub.3                                                                          OCH.sub.3                                         H    N(CH.sub.2 CN).sub.2                                                                        O  H CH.sub.3                                                                          OCH.sub.3                                         H    N(CH.sub.2 CH.sub.2 CN).sub.2                                                               O  H CH.sub.3                                                                          OCH.sub.3                                         H    N(C.sub.2 H.sub.5).sub.2                                                                    O  H CH.sub.3                                                                          OCH.sub.3                                         H                                                                                   ##STR351##   O  H CH.sub.3                                                                          OCH.sub.3                                         __________________________________________________________________________

                  TABLE VIII-a                                                    ______________________________________                                         ##STR352##                                                                   A'   QR.sup.I    W      R.sub.5                                                                           X.sub.1                                                                              Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3   O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H   CH.sub.3                                                                             CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H   CH.sub.3                                                                             CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H   CH.sub.3                                                                             CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H   CH.sub.3                                                                             CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H   OCH.sub.3                                                                            OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H   OCH.sub.3                                                                            OCH.sub.3                                        ##STR353## O      H   OCH.sub.3                                                                            OCH.sub.3                                  H                                                                                   ##STR354## O      H   OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-b                                                    ______________________________________                                         ##STR355##                                                                   A'   QR.sup.I    W      R.sub.5                                                                           X.sub.1                                                                              Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3   O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H   CH.sub.3                                                                             CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H   CH.sub.3                                                                             CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H   CH.sub.3                                                                             CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H   CH.sub.3                                                                             CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H   OCH.sub.3                                                                            OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H   OCH.sub.3                                                                            OCH.sub.3                                        ##STR356## O      H   OCH.sub.3                                                                            OCH.sub.3                                  H                                                                                   ##STR357## O      H   OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-c                                                    ______________________________________                                         ##STR358##                                                                   A'   QR.sup.I    W      R.sub.5                                                                           X.sub.1                                                                              Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3   O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H   CH.sub.3                                                                             CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H   CH.sub.3                                                                             CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H   CH.sub.3                                                                             CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H   CH.sub.3                                                                             CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H   OCH.sub.3                                                                            OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H   OCH.sub.3                                                                            OCH.sub.3                                        ##STR359## O      H   OCH.sub.3                                                                            OCH.sub.3                                  H                                                                                   ##STR360## O      H   OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-d                                                    ______________________________________                                         ##STR361##                                                                   A'   QR.sup.I    W      R.sub.5                                                                           X.sub.1                                                                              Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3   O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H   CH.sub.3                                                                             CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H   CH.sub.3                                                                             CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H   CH.sub.3                                                                             CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H   CH.sub.3                                                                             CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H   OCH.sub.3                                                                            OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H   OCH.sub.3                                                                            OCH.sub.3                                        ##STR362## O      H   OCH.sub.3                                                                            OCH.sub.3                                  H                                                                                   ##STR363## O      H   OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-e                                                    ______________________________________                                         ##STR364##                                                                   A'   QR.sup.I    W      R.sub.5                                                                           X.sub.1                                                                              Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3   O      H   CH.sub.3                                                                             CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H   CH.sub.3                                                                             CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H   CH.sub.3                                                                             CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H   CH.sub.3                                                                             CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H   CH.sub.3                                                                             CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H   OCH.sub.3                                                                            OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H   OCH.sub.3                                                                            OCH.sub.3                                        ##STR365## O      H   OCH.sub.3                                                                            OCH.sub.3                                  H                                                                                   ##STR366## O      H   OCH.sub.3                                                                            OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-f                                                    ______________________________________                                         ##STR367##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR368## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR369## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-g                                                    ______________________________________                                         ##STR370##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR371## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR372## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-h                                                    ______________________________________                                         ##STR373##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR374## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR375## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-i                                                    ______________________________________                                         ##STR376##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR377## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR378## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-j                                                    ______________________________________                                         ##STR379##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR380## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR381## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-k                                                    ______________________________________                                         ##STR382##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR383## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR384## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE VIII-1                                                    ______________________________________                                         ##STR385##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            X.sub.1                                                                             Y.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.3                                   H    SCH.sub.3 CH.sub.3                                                                        O      H    CH.sub.3                                                                            CH.sub.3                                   H    S(CH.sub.2).sub.3 CH.sub.3                                                                O      H    CH.sub.3                                                                            CH.sub.3                                   H    NH(CH.sub.2).sub.3 CH.sub.3                                                               O      H    CH.sub.3                                                                            CH.sub.3                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.3                                   H    N(CH.sub.3).sub.2                                                                         O      H    OCH.sub.3                                                                           OCH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O      H    OCH.sub.3                                                                           OCH.sub.3                                        ##STR386## O      H    OCH.sub.3                                                                           OCH.sub.3                                  H                                                                                   ##STR387## O      H    OCH.sub.3                                                                           OCH.sub.3                                  ______________________________________                                    

                  TABLE IX-a                                                      ______________________________________                                         ##STR388##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            Y.sub.1                                                                             X.sub.11                                                                            m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.2                                   H    SC.sub.2 H.sub.5                                                                          O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH.sub.2 CHCH.sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHC.sub.2 H.sub.5                                                                         O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    N(CH.sub.3).sub.2                                                                         O      H    CH.sub.3                                                                            O                                          ______________________________________                                    

                  TABLE IX-b                                                      ______________________________________                                         ##STR389##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            Y.sub.1                                                                             X.sub.11                                                                            m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.2                                   H    SC.sub.2 H.sub.5                                                                          O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH.sub.2 CHCH.sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHC.sub.2 H.sub.5                                                                         O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    N(CH.sub.3).sub.2                                                                         O      H    CH.sub.3                                                                            O                                          ______________________________________                                    

                  TABLE IX-c                                                      ______________________________________                                         ##STR390##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            Y.sub.1                                                                             X.sub.11                                                                            m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.2                                   H    SC.sub.2 H.sub.5                                                                          O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH.sub.2 CHCH.sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHC.sub.2 H.sub.5                                                                         O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    N(CH.sub.3).sub.2                                                                         O      H    CH.sub.3                                                                            O                                          ______________________________________                                    

                  TABLE IX-d                                                      ______________________________________                                         ##STR391##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            Y.sub.1                                                                             X.sub.11                                                                            m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.2                                   H    SC.sub.2 H.sub.5                                                                          O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH.sub.2 CHCH.sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHC.sub.2 H.sub.5                                                                         O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    N(CH.sub.3).sub.2                                                                         O      H    CH.sub.3                                                                            O                                          ______________________________________                                    

                  TABLE IX-e                                                      ______________________________________                                         ##STR392##                                                                   A'   QR.sup.I    W      R.sub.5                                                                            Y.sub.1                                                                             X.sub.11                                                                            m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O      H    CH.sub.3                                                                            CH.sub.2                                   H    SC.sub.2 H.sub.5                                                                          O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH(CH.sub.3).sub.2                                                                       O      H    CH.sub.3                                                                            CH.sub.2                                   H    SCH.sub.2 CHCH.sub.2                                                                      O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHC.sub.2 H.sub.5                                                                         O      H    CH.sub.3                                                                            CH.sub.2                                   H    NHCH(CH.sub.3).sub.2                                                                      O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O      H    CH.sub.3                                                                            O                                          H    N(CH.sub.3).sub.2                                                                         O      H    CH.sub.3                                                                            O                                          ______________________________________                                    

                  TABLE IX-f                                                      ______________________________________                                         ##STR393##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           Y.sub.1                                                                              X.sub.11                                                                           m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.2                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.2                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.2                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.2                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.2                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             O                                         H    NH(CH.sub.2).sub.5 CH.sub.3                                                               O       H   CH.sub.3                                                                             O                                         H    NH(CH.sub.2).sub.8 CH.sub.3                                                               O       H   CH.sub.3                                                                             O                                         H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             O                                         ______________________________________                                    

                  TABLE X-a                                                       ______________________________________                                         ##STR394##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           X      Y    m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.3                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2).sub.3 CH.sub.3                                                                O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2)CH.sub.3                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(C.sub.2 H.sub. 5).sub.2                                                                 O       H   CH.sub.3                                                                             CH.sub.3                                  ______________________________________                                    

                  TABLE X-b                                                       ______________________________________                                         ##STR395##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           X      Y    m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.3                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2).sub.3 CH.sub.3                                                                O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2)CH.sub.3                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(C.sub.2 H.sub. 5).sub.2                                                                 O       H   CH.sub.3                                                                             CH.sub.3                                  ______________________________________                                    

                  TABLE X-c                                                       ______________________________________                                         ##STR396##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           X      Y    m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.3                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2).sub.3 CH.sub.3                                                                O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2)CH.sub.3                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(C.sub.2 H.sub.5).sub.2                                                                  O       H   CH.sub.3                                                                             CH.sub.3                                  ______________________________________                                    

                  TABLE X-d                                                       ______________________________________                                         ##STR397##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           X      Y    m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.3                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2).sub.3 CH.sub.3                                                                O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2)CH.sub.3                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(C.sub.2 H.sub. 5).sub.2                                                                 O       H   CH.sub.3                                                                             CH.sub.3                                  ______________________________________                                    

                  TABLE X-e                                                       ______________________________________                                         ##STR398##                                                                   A'   QR.sup.I    W       R.sub.5                                                                           X      Y    m.p. (°C.)                    ______________________________________                                        H    SCH.sub.3   O       H   CH.sub.3                                                                             CH.sub.3                                  H    SC.sub.2 H.sub.5                                                                          O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH(CH.sub.3).sub.2                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2).sub.3 CH.sub.3                                                                O       H   CH.sub.3                                                                             CH.sub.3                                  H    SCH.sub.2 CHCH.sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    S(CH.sub.2)CH.sub.3                                                                       O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHCH(CH.sub.3).sub.2                                                                      O       H   CH.sub.3                                                                             CH.sub.3                                  H    NHC.sub.2 H.sub.5                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(CH.sub.3).sub.2                                                                         O       H   CH.sub.3                                                                             CH.sub.3                                  H    N(C.sub.2 H.sub.5).sub. 2                                                                 O       H   CH.sub.3                                                                             CH.sub.3                                  ______________________________________                                    

                  TABLE X-f                                                       ______________________________________                                         ##STR399##                                                                   A'    QR.sup.I    W     R.sub.5                                                                             X    Y     m.p. (°C.)                    ______________________________________                                        H     SCH.sub.3   O     H     CH.sub.3                                                                           CH.sub.3                                   H     SC.sub.2 H.sub.5                                                                          O     H     CH.sub.3                                                                           CH.sub.3                                   H     SCH(CH.sub.3).sub.2                                                                       O     H     CH.sub.3                                                                           CH.sub.3                                   H     S(CH.sub.2).sub.3 CH.sub.3                                                                O     H     CH.sub.3                                                                           CH.sub.3                                   H     SCH.sub.2 CHCH.sub.2                                                                      O     H     CH.sub.3                                                                           CH.sub.3                                   H     S(CH.sub.2)CH.sub.3                                                                       O     H     CH.sub.3                                                                           CH.sub.3                                   H     NHCH(CH.sub.3).sub.2                                                                      O     H     CH.sub.3                                                                           CH.sub.3                                   H     NHC.sub.2 H.sub.5                                                                         O     H     CH.sub.3                                                                           CH.sub.3                                   H     N(CH.sub.3).sub.2                                                                         O     H     CH.sub.3                                                                           CH.sub.3                                   H     N(C.sub.2 H.sub.5).sub.2                                                                  O     H     CH.sub.3                                                                           CH.sub.3                                   ______________________________________                                    

                  TABLE XI-a                                                      ______________________________________                                         ##STR400##                                                                   ______________________________________                                         A'                                                                                ##STR401##       W     R.sub.5                                                                            X     Y     (°C.)m.p.                 ______________________________________                                             ##STR402##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR403##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR404##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR405##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR406##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR407##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR408##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR409##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR410##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR411##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR412##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR413##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR414##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR415##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR416##      O     H    CH.sub.3                                                                            CH.sub.3                                ______________________________________                                         A'                                                                                ##STR417##       W     R.sub.5                                                                            X     Y     (°C.)m.p.                 ______________________________________                                             ##STR418##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR419##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR420##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR421##                                                               H                                                                                  ##STR422##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR423##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR424##      O     H    OCH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-b                                                      ______________________________________                                         ##STR425##                                                                    A'                                                                                ##STR426##       W     R.sub.5                                                                            X    Y     (°C.)m.p.                  ______________________________________                                             ##STR427##      O     H    CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR428##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR429##      O     H    CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR430##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR431##      O     H    CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR432##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR433##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR434##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR435##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR436##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR437##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR438##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR439##      O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR440##      O     H    CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR441##      O     H    CH.sub.3                                                                           CH.sub.3                                 H                                                                                  ##STR442##      O     H    CH.sub.3                                                                           OCH.sub.3                                ______________________________________                                    

                  TABLE XI-c                                                      ______________________________________                                         ##STR443##                                                                    A'                                                                                ##STR444##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR445##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR446##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR447##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR448##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR449##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR450##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR451##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR452##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR453##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR454##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR455##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR456##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR457##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR458##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR459##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR460##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-d                                                      ______________________________________                                         ##STR461##                                                                    A'                                                                                ##STR462##         W R.sub.5                                                                             X    Y     (°C.)m.p.                   ______________________________________                                             ##STR463##        O H     CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR464##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR465##        O H     CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR466##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR467##        O H     CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR468##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR469##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR470##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR471##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR472##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR473##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR474##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR475##        O CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR476##        O H     CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR477##        O H     CH.sub.3                                                                           CH.sub.3                                  H                                                                                  ##STR478##        O H     CH.sub.3                                                                           OCH.sub.3                                 H                                                                                  ##STR479##        O H     CH.sub.3                                                                           CH.sub.3                                                                            155-  158°                   ______________________________________                                    

                  TABLE XI-e                                                      ______________________________________                                         ##STR480##                                                                    A'                                                                                ##STR481##         W     R.sub.5                                                                            X    Y    (°C.) m.p.                ______________________________________                                             ##STR482##        O     H    CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR483##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR484##        O     H    CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR485##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR486##        O     H    CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR487##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR488##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR489##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR490##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR491##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR492##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR493##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR494##        O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR495##        O     H    CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR496##        O     H    CH.sub.3                                                                           CH.sub.3                               H                                                                                  ##STR497##        O     H    CH.sub.3                                                                           OCH.sub.3                              ______________________________________                                    

                  TABLE XI-f                                                      ______________________________________                                         ##STR498##                                                                    A'                                                                                ##STR499##          W     R.sub.5                                                                            X    Y   (°C.) m.p.                ______________________________________                                             ##STR500##         O     H    CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR501##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR502##         O     H    CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR503##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR504##         O     H    CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR505##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR506##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR507##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR508##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR509##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR510##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR511##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR512##         O     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR513##         O     H    CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR514##         O     H    CH.sub.3                                                                           CH.sub.3                              H                                                                                  ##STR515##         O     H    CH.sub.3                                                                           OCH.sub.3                             ______________________________________                                    

                  TABLE XI-g                                                      ______________________________________                                         ##STR516##                                                                    A'                                                                                ##STR517##       W     R.sub.5                                                                            X     Y     (°C.)m.p.                 ______________________________________                                             ##STR518##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR519##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR520##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR521##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR522##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR523##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR524##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR525##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR526##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR527##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR528##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR529##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR530##      O     CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR531##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR532##      O     H    CH.sub.3                                                                            CH.sub.3                                H                                                                                  ##STR533##      O     H    OCH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-h                                                      ______________________________________                                         ##STR534##                                                                    A'                                                                                ##STR535##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR536##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR537##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR538##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR539##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR540##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR541##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR542##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR543##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR544##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR545##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR546##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR547##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR548##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR549##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR550##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR551##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-i                                                      ______________________________________                                         ##STR552##                                                                    A'                                                                                ##STR553##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR554##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR555##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR556##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR557##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR558##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR559##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR560##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR561##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR562##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR563##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR564##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR565##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR566##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR567##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR568##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR569##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-j                                                      ______________________________________                                         ##STR570##                                                                    A'                                                                                ##STR571##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR572##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR573##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR574##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR575##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub. 3                               H                                                                                  ##STR576##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR577##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR578##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR579##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR580##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR581##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR582##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR583##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR584##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR585##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR586##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR587##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-k                                                      ______________________________________                                         ##STR588##                                                                    A'                                                                                ##STR589##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR590##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR591##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR592##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR593##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR594##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR595##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR596##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR597##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR598##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR599##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR600##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR601##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR602##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR603##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR604##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR605##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XI-l                                                      ______________________________________                                         ##STR606##                                                                    A'                                                                                ##STR607##       W      R.sub.5                                                                            X    Y     (°C.)m.p.                 ______________________________________                                             ##STR608##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR609##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR610##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR611##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR612##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR613##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR614##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR615##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR616##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR617##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR618##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR619##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR620##      O      CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR621##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR622##      O      H    CH.sub.3                                                                           CH.sub.3                                H                                                                                  ##STR623##      O      H    CH.sub.3                                                                           OCH.sub.3                               ______________________________________                                    

                  TABLE XII                                                       ______________________________________                                         Other compounds within the scope of this invention include:                  ______________________________________                                         ##STR624##                                                                    ##STR625##                                                                    ##STR626##                                                                    ##STR627##                                                                    ##STR628##                                                                    ##STR629##                                                                    ##STR630##                                                                    ##STR631##                                                                    ##STR632##                                                                    ##STR633##                                                                    ##STR634##                                                                    ##STR635##                                                                    ##STR636##                                                                    ##STR637##                                                                    ##STR638##                                                                    ##STR639##                                                                    ##STR640##                                                                   ______________________________________                                    

                  TABLE XII-a                                                     ______________________________________                                         ##STR641##                                                                   A'         W'      W     R.sup.I                                              ______________________________________                                        H          S       O     C.sub.2 H.sub.5                                      H          S       O     CH(CH.sub.3).sub.2                                   H          S       O     CH.sub.2 CH.sub.2 Cl                                 H          S       O     (CH.sub.2).sub.6 H                                   H          S       O                                                                                    ##STR642##                                          H          S       O     CH.sub.2CHCH.sub.2                                   H          S       O     CH.sub.2CHCHCH.sub.3                                 H          S       O     CH.sub.2 CHCHCH.sub.2 CH.sub.3                       H          S       O                                                                                    ##STR643##                                          H          S       O     CH.sub.2 CH(CH.sub.3).sub.2                          H          S       O     CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                 H          S       O     CH.sub.2 CH.sub.2 Cl                                 H          S       O     CH.sub.2 CH(CH.sub.2 Cl).sub.2                       H          S       O     CH.sub.2 OCl.sub.3                                   H          S       O     (CH.sub.2).sub.6 Cl                                  H          S       O     (CH.sub.2).sub.6 Br                                  H          S       O     CH.sub.2 CH.sub.2 Br                                 H          S       O     (CH.sub.2).sub.6 F                                   H          S       O     (CH.sub.2).sub.4 F                                   H          S       O     CH.sub.2 CN                                          H          S       O     CH.sub.2 CH.sub.2 CN                                 H          S       O     CH.sub.2 CH.sub.2 OCH.sub.3                          H          S       O     (CH.sub.2).sub.6 OCH.sub.3                           H          S       O     (CH.sub.2).sub.3 OCH.sub.3                           H          S       O                                                                                    ##STR644##                                          H          S       O                                                                                    ##STR645##                                          H          S       O                                                                                    ##STR646##                                          H          S       O                                                                                    ##STR647##                                          H          S       O     CH.sub.2 CN                                          H          S       O                                                                                    ##STR648##                                          H          S       O                                                                                    ##STR649##                                          H          S       O                                                                                    ##STR650##                                          H          S       O                                                                                    ##STR651##                                          H          S       O                                                                                    ##STR652##                                          H          S       O                                                                                    ##STR653##                                          H          S       O                                                                                    ##STR654##                                          H          S       O                                                                                    ##STR655##                                          H          S       O     CH.sub.2 OCH.sub.3                                   H          S       O     CH.sub.2 OC.sub.2 H.sub.5                            H          S       O     CH.sub.2 O(CH.sub.2).sub.4 H                         H          S       O     CH.sub.2 CHCHCl                                      H          S       O     CH.sub.2 CHCHCH.sub.2 Cl                             H          S       O     CH.sub.2 CHCH(CH.sub.2).sub.3 Cl                     H          S       O     CH.sub.2 CCCH.sub.3                                  H          S       O     CH.sub.2 CCCH.sub.2 Cl                               H          S       O     CH.sub.2 CCCH.sub.2 CH.sub.2Cl                       H          S       O                                                                                    ##STR656##                                          H          S       O                                                                                    ##STR657##                                          H          S       O                                                                                    ##STR658##                                          H          S       O                                                                                    ##STR659##                                          H          S       O                                                                                    ##STR660##                                          H          S       O                                                                                    ##STR661##                                          H          S       O                                                                                    ##STR662##                                          H          S       O                                                                                    ##STR663##                                          H          S       O                                                                                    ##STR664##                                          H          S       O                                                                                    ##STR665##                                          H          S       O                                                                                    ##STR666##                                          H          S       O                                                                                    ##STR667##                                          H          S       O                                                                                    ##STR668##                                          H          S       O                                                                                    ##STR669##                                          H          S       O                                                                                    ##STR670##                                          H          S       O     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                 H          S       O     CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                H          S       O                                                                                    ##STR671##                                          H          S       O     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl              H          S       O     CH.sub.2 CH.sub.2 OCH.sub.2 CCl.sub.3                H          S       O                                                                                    ##STR672##                                          H          S       O                                                                                    ##STR673##                                          H          S       O     (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                 H          S       O     (CH.sub.2).sub.3 OCH.sub.2 CH.sub.3                  H          S       O     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3       H          S       O     CH.sub.2 CH.sub.2 (OCH.sub.2 CH.sub.2).sub.2                                  OC.sub.2 H.sub.5                                     5-CH.sub.3 S       O     CH.sub.3                                             H          O       O     CH.sub.3                                             H          S       S     CH.sub.3                                             4-CH.sub.3 S       O     CH.sub.3                                             4-Cl       S       O     CH.sub.3                                             4-Br       S       O     CH.sub.3                                             5-Br       S       O     CH.sub.3                                             4-NO.sub.2 S       O     CH.sub.3                                             4-C.sub.2 H.sub.5                                                                        S       O     CH.sub.3                                             5-C.sub.2 H.sub.5                                                                        S       O     CH.sub.3                                             5- -n-C.sub.7 H.sub.9                                                                    S       O     CH.sub.3                                             5-CH(CH.sub.3).sub.2                                                                     S       O     CH.sub.3                                             4-CF.sub.3 S       O     CH.sub.3                                             5-OCH.sub.3                                                                              S       O     CH.sub.3                                             ______________________________________                                    

                  TABLE XII-b                                                     ______________________________________                                         ##STR674##                                                                   A'          W'     W      R.sup.I                                             ______________________________________                                        H           S      O      C.sub.2 H.sub.5                                     H           S      O      CH(CH.sub.3).sub.2                                  H           S      O      CH.sub.2 CH.sub.2 Cl                                H           S      O      (CH.sub.2).sub.6 H                                  H           S      O                                                                                     ##STR675##                                         H           S      O      CH.sub.2CHCH.sub.2                                  H           S      O      CH.sub.2CHCHCH.sub.3                                H           S      O      CH.sub.2 CHCHCH.sub.2 CH.sub.3                      H           S      O                                                                                     ##STR676##                                         H           S      O      CH.sub.2 CH(CH.sub.3).sub.2                         H           S      O      CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                H           S      O      CH.sub.2 CH.sub.2 Cl                                H           S      O      CH.sub.2 CH(CH.sub.2 Cl).sub.2                      H           S      O      CH.sub.2 CCl.sub.3                                  H           S      O      (CH.sub.2).sub.6 Cl                                 H           S      O      (CH.sub.2).sub.6 Br                                 H           S      O      CH.sub.2 CH.sub.2 Br                                H           S      O      (CH.sub.2).sub.6 F                                  H           S      O      (CH.sub.2).sub.4 F                                  H           S      O      CH.sub.2 CN                                         H           S      O      CH.sub.2 CH.sub.2 CN                                H           S      O      CH.sub.2 CH.sub.2 OCH.sub.3                         H           S      O      (CH.sub.2).sub.6 OCH.sub.3                          H           S      O      (CH.sub.2).sub.3 OCH.sub.3                          H           S      O                                                                                     ##STR677##                                         H           S      O                                                                                     ##STR678##                                         H           S      O                                                                                     ##STR679##                                         H           S      O                                                                                     ##STR680##                                         H           S      O      CH.sub.2 CN                                         H           S      O                                                                                     ##STR681##                                         H           S      O                                                                                     ##STR682##                                         H           S      O                                                                                     ##STR683##                                         H           S      O                                                                                     ##STR684##                                         H           S      O                                                                                     ##STR685##                                         H           S      O                                                                                     ##STR686##                                         H           S      O                                                                                     ##STR687##                                         H           S      O                                                                                     ##STR688##                                         H           S      O      CH.sub.2 OCH.sub.3                                  H           S      O      CH.sub.2 OC.sub.2 H.sub.5                           H           S      O      CH.sub.2 O(CH.sub.2).sub.4 H                        H           S      O      CH.sub.2 CHCHCl                                     H           S      O      CH.sub.2 CHCHCH.sub.2 Cl                            H           S      O      CH.sub.2 CHCH(CH.sub.2).sub.3 Cl                    H           S      O      CH.sub.2 CCCH.sub.3                                 H           S      O      CH.sub.2 CCCH.sub.2 Cl                              H           S      O      CH.sub.2 CCCH.sub.2 CH.sub.2Cl                      H           S      O                                                                                     ##STR689##                                         H           S      O                                                                                     ##STR690##                                         H           S      O                                                                                     ##STR691##                                         H           S      O                                                                                     ##STR692##                                         H           S      O                                                                                     ##STR693##                                         H           S      O                                                                                     ##STR694##                                         H           S      O                                                                                     ##STR695##                                         H           S      O                                                                                     ##STR696##                                         H           S      O                                                                                     ##STR697##                                         H           S      O                                                                                     ##STR698##                                         H           S      O                                                                                     ##STR699##                                         H           S      O                                                                                     ##STR700##                                         H           S      O                                                                                     ##STR701##                                         H           S      O                                                                                     ##STR702##                                         H           S      O                                                                                     ##STR703##                                         H           S      O      CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                H           S      O      CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2               H           S      O                                                                                     ##STR704##                                         H           S      O      CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl             H           S      O      CH.sub.2 CH.sub.2 OCH.sub.2 CCl.sub.3               H           S      O                                                                                     ##STR705##                                         H           S      O                                                                                     ##STR706##                                         H           S      O      (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                H           S      O      (CH.sub.2).sub.3 OCH.sub.2 CH.sub.3                 H           S      O      CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3      H           S      O      CH.sub.2 CH.sub.2 (OCH.sub.2 CH.sub.2).sub.2                                  OC.sub.2 H.sub.5                                    5-CH.sub.3  S      O      CH.sub.3                                            H           O      O      CH.sub.3                                            H           S      S      CH.sub.3                                            2-CH.sub.3  S      O      CH.sub.3                                            2-Cl        S      O      CH.sub.3                                            2-Br        S      O      CH.sub.3                                            5-Br        S      O      CH.sub.3                                            2-NO.sub.2  S      O      CH.sub.3                                            2-C.sub.2 H.sub.5                                                                         S      O      CH.sub.3                                            5-C.sub.2 H.sub.5                                                                         S      O      CH.sub.3                                            5- -n-C.sub.7 H.sub.9                                                                     S      O      CH.sub.3                                            5-CH(CH.sub.3).sub.2                                                                      S      O      CH.sub.3                                            2-CF.sub.3  S      O      CH.sub.3                                            5-OCH.sub.3 S      O      CH.sub.3                                            ______________________________________                                    

                  TABLE XII-c                                                     ______________________________________                                         ##STR707##                                                                   A'          W'    W       R.sup.I                                             ______________________________________                                        H           S     O       C.sub.2 H.sub.5                                     H           S     O       CH(CH.sub.3).sub.2                                  H           S     O       CH.sub.2 CH.sub.2 Cl                                H           S     O       (CH.sub.2).sub.6 H                                  H           S     O                                                                                      ##STR708##                                         H           S     O       CH.sub.2CHCH.sub.2                                  H           S     O       CH.sub.2CHCHCH.sub.3                                H           S     O       CH.sub.2 CHCHCH.sub.2 CH.sub.3                      H           S     O                                                                                      ##STR709##                                         H           S     O       CH.sub.2 CH(CH.sub.3).sub.2                         H           S     O       CH.sub.2 CH(CH.sub.2 CH.sub.3).sub.2                H           S     O       CH.sub.2 CH.sub.2 Cl                                H           S     O       CH.sub.2 CH(CH.sub.2 Cl).sub.2                      H           S     O       CH.sub.2 CCl.sub.3                                  H           S     O       (CH.sub.2).sub.6 Cl                                 H           S     O       (CH.sub.2).sub.6 Br                                 H           S     O       CH.sub.2 CH.sub.2 Br                                H           S     O       (CH.sub.2).sub.6 F                                  H           S     O       (CH.sub.2).sub.4 F                                  H           S     O       CH.sub.2 CN                                         H           S     O       CH.sub.2 CH.sub.2 CN                                H           S     O       CH.sub.2 CH.sub.2 OCH.sub.3                         H           S     O       (CH.sub.2).sub.6 OCH.sub.3                          H           S     O       (CH.sub.2).sub.3 OCH.sub.3                          H           S     O                                                                                      ##STR710##                                         H           S     O                                                                                      ##STR711##                                         H           S     O                                                                                      ##STR712##                                         H           S     O                                                                                      ##STR713##                                         H           S     O       CH.sub.2 CN                                         H           S     O                                                                                      ##STR714##                                         H           S     O                                                                                      ##STR715##                                         H           S     O                                                                                      ##STR716##                                         H           S     O                                                                                      ##STR717##                                         H           S     O                                                                                      ##STR718##                                         H           S     O                                                                                      ##STR719##                                         H           S     O                                                                                      ##STR720##                                         H           S     O                                                                                      ##STR721##                                         H           S     O       CH.sub.2 OCH.sub.3                                  H           S     O       CH.sub.2 OC.sub.2 H.sub.5                           H           S     O       CH.sub.2 O(CH.sub.2).sub.4 H                        H           S     O       CH.sub.2 CHCHCl                                     H           S     O       CH.sub.2 CHCHCH.sub.2 Cl                            H           S     O       CH.sub.2 CHCH(CH.sub.2).sub.3 Cl                    H           S     O       CH.sub.2 CCCH.sub.3                                 H           S     O       CH.sub.2 CCCH.sub.2 Cl                              H           S     O       CH.sub.2 CCCH.sub.2 CH.sub.2Cl                      H           S     O                                                                                      ##STR722##                                         H           S     O                                                                                      ##STR723##                                         H           S     O                                                                                      ##STR724##                                         H           S     O                                                                                      ##STR725##                                         H           S     O                                                                                      ##STR726##                                         H           S     O                                                                                      ##STR727##                                         H           S     O                                                                                      ##STR728##                                         H           S     O                                                                                      ##STR729##                                         H           S     O                                                                                      ##STR730##                                         H           S     O                                                                                      ##STR731##                                         H           S     O                                                                                      ##STR732##                                         H           S     O                                                                                      ##STR733##                                         H           S     O                                                                                      ##STR734##                                         H           S     O                                                                                      ##STR735##                                         H           S     O                                                                                      ##STR736##                                         H           S     O       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                H           S     O       CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2               H           S     O                                                                                      ##STR737##                                         H           S     O       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl             H           S     O       CH.sub.2 CH.sub.2 OCH.sub.2 CCl.sub.3               H           S     O                                                                                      ##STR738##                                         H           S     O                                                                                      ##STR739##                                         H           S     O       (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                H           S     O       (CH.sub.2).sub.3 OCH.sub.2 CH.sub.3                 H           S     O       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3      H           S     O       CH.sub.2 CH.sub.2 (OCH.sub.2 CH.sub.2).sub.2                                  OC.sub.2 H.sub.5                                    5-CH.sub.3  S     O       CH.sub.3                                            H           O     O       CH.sub.3                                            H           S     S       CH.sub.3                                            4-CH.sub.3  S     O       CH.sub.3                                            4-Cl        S     O       CH.sub.3                                            4-Br        S     O       CH.sub.3                                            5-Br        S     O       CH.sub.3                                            4-NO.sub.2  S     O       CH.sub.3                                            4-C.sub.2 H.sub.5                                                                         S     O       CH.sub.3                                            5-C.sub.2 H.sub.5                                                                         S     O       CH.sub.3                                            5- -n-C.sub.7 H.sub.9                                                                     S     O       CH.sub.3                                            5-CH(CH.sub.3).sub.2                                                                      S     O       CH.sub.3                                            4-CF.sub.3  S     O       CH.sub.3                                            5-OCH.sub.3 S     O       CH.sub.3                                            ______________________________________                                    

                  TABLE XII-d                                                     ______________________________________                                         ##STR740##                                                                   X             Y            m.p. (°C.)                                  ______________________________________                                        CH.sub.3      OCH.sub.3    182-187(d)                                         OCH.sub.3     OCH.sub.3    195-197                                            ______________________________________                                    

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectate. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions set forth in Table XVIII.

                  TABLE XVIII                                                     ______________________________________                                                  Active   Weight Percent*                                                      Ingredient                                                                             Diluent(s) Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                          20-90       0-74      1-10                                        Oil Suspensions,                                                                           3-50      40-95      0-15                                        Emulsions, Solu-                                                              tions (including                                                              Emulsifiable                                                                  Concentrates)                                                                 Aqueous Suspension                                                                        10-50      40-84      1-20                                        Dusts        1-25      70-99      0-5                                         Granules and                                                                              0.1-95       5-99.9   0-15                                        Pellets                                                                       High Strength                                                                             90-99       0-10      0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredients can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers," 2nd Ed., Dorland Books,Caldwell, N.J. but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual," MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents," Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbilogical growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration," ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook," 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167, 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 7

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        methyl 3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                                                     80%                                              aminosulfonyl]-2- thiophenecarboxylate                                        sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 8

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        methyl 3-[[(4,6-dimethoxypyrimidin-2-yl)-                                                                50%                                                aminocarbonyl]aminosulfonyl]-2-thiophene-                                     carboxylate                                                                   sodium alkylnaphthalenesulfonate                                                                         2%                                                 low viscosity methyl cellulose                                                                           2%                                                 diatomaceous earth         46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 9

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 8                                                                            5%                                                  attapulgite granules      95%                                                 (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 10

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)-                                                             25%                                              aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate                           anhydrous sodium sulfate     10%                                              crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite  59%                                              ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S. Ser.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 11

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        methyl 3-[[(4,6-dimethylpyrimidin-2-yl)amino-                                                             25%                                               carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                polyoxyethylene sorbitol hexaoleate                                                                       5%                                                highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingsuspension may be applied directly, but preferably after being extendedwith oils or emulsified in water.

EXAMPLE 12

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        methyl 3-[[(4,6-dimethoxypyrimidin-2-yl)amino-                                                            20%                                               carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                sodium alkylnaphthalenesulfonate                                                                          4%                                                sodium ligninsulfonate      4%                                                low viscosity methyl cellulose                                                                            3%                                                attapulgite                 69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 13

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)-                                                             35%                                              aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate                           blend of polyalcohol carboxylic                                                                            6%                                               esters and oil soluble petroleum                                              sulfonates                                                                    xylene                       59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 3 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 14

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        methyl 3-[[(4,6-dimethylpyrimidin-2-yl)amino-                                                             99%                                               carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                silica aerogel              0.5%                                              synthetic amorphous silica  0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 15

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        methyl 3-[[(4,6-dimethoxypyrimidin-2-yl)amino-                                                            1%                                                carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                N,N--dimethylformamide      9%                                                attapulgite granules        90%                                               (U.S.S. 20-40 mesh).                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a rotating blender. After spraying ofthe solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 16

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)-                                                             40%                                              aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate                           polyacrylic acid thickener   0.3%                                             dodecylphenol polyethylene glycol ether                                                                    0.5%                                             disodium phosphate           1%                                               monosodium phosphate         0.5%                                             polyvinyl alcohol            1.0%                                             water                        56.7%                                            ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 17

    ______________________________________                                        Solution                                                                      ______________________________________                                        methyl 3-[[(4,6-dimethylpyrimidin-2-yl)amino-                                                             5%                                                carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 18

    ______________________________________                                        Granule                                                                       ______________________________________                                        methyl 3-[[(4,6-dimethoxypyrimidin-2-yl)amino-                                                            80%                                               carbonyl]aminosulfonyl]-2-thiophenecarboxylate                                wetting agent               1%                                                crude ligninsulfonate salt (containing                                                                    10%                                               5-20% of the natural sugars)                                                  attapulgite clay            9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 19

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)-                                                             0.1%                                             aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylate                           attapulgite granules         99.9%                                            (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double cond blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

UTILITY

The compounds of the present invention are powerful herbicides. Theyhave utility for broad-spectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for theselective pre- or post-emergence weed control in crops, such as wheatand soybeans.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the tupes of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.06 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for selective weed control orfor situations where only short-term persistance is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures are results follow.

TEST A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), Cassia tora, morningglory (Ipomoeaspp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat aswell as nutsedge tubers were planted in a growth medium and treatedpreemergence with the chemicals dissolved in a non-phytotoxic solvent.At the same time, cotton having five leaves (including cotyledonaryones), bush beans with the third trifoliate leaf expanding, crabgrass,barnyardgrass and wild oats with two leaves, cassia with three leaves(including cotyledonary ones), morningglory and cocklebur with fourleaves (including the cotyledonary ones), sorghum and corn with fourleaves, soybean with two cotyledonary leaves, rice with three leaves,wheat with one leaf, and nutsedge with three-five leaves were sprayed.Treated plants and controls were maintained in a greenhouse for sixteendays, whereupon all species were compared to controls and visually ratedfor response to treatment. The ratings are based on a numerical scaleextending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings: B=burn; G=growthretardation; C=chlorosis/necrosis; D=defoliation; 6Y=abscised buds orflowers; 6F=delayed flowering; U=unusual pigmentation; S=albinism;E=emergence inhibition; and H=formative effects. The ratings for thecompounds tested by this procedure are presented in Table A. It will beseen that certain of the compounds tested have utility for selectivepre- and post-emergence weed control in soybeans and wheat.

    TABLE A         MORN-     BARN-        BUSH- COT- ING- COCK- CAS- NUT- CRAB- YARD-     WILD   SOY-  SOR- kg/ha BEAN TON GLORY LEBUR SIA SEDGE GRASS GRASS OATS     WHEAT CORN BEAN RICE GHUM       POST EMERGENCE      ##STR741##      0.1 6C,9G,6Y 3U,9G 9C 5C,9G 0 5C,9G 5C,9G 6C,9G 2G 1C,9G 1C,9H 3G 2C,9G     1C,9G      ##STR742##      0.1 5C,8G,6Y 7C,9G 10C 9C 2C 1C,9G 3C,8G 9C 1C,7G 2C,8G 2U,9G 5C,9G     5C,9G 5U,9G      ##STR743##      0.1 8D,9G,6Y 7C,9G 10C 3C,9G 1C,3G 4C,9G 6C,9G 9C 2C,8G 3C,7G 1C,9G     2C,8G 3C,9G 3C,9G      ##STR744##      0.1 9C 3C,7G 5C,8G 10C 1C 0 1C,5G 2C,8H 0 0 2C,8H 1C,2H -- 1C,9G      ##STR745##      0.4 6C,9G 3C,3H 1C,3H 1C,5G 2C,2H 1C 4G 2C,5H 0 0 2C,7H 2C,3G 1C,5G     2C,9H      ##STR746##      0.1 2C,8G,6Y 9C 10C 10C 2C,7H 1C 1C 2C,9H 1H 1H 9H 5C,9G 2C,8G 2C,7H      ##STR747##      0.1 9C 9C 10C 6C 1C 1C 3C 10C 0 0 7C 2C 5C 9G      ##STR748##      0.4 3C,4G,6F 1C,7G 10C 10C 0 5C,5G 10C 10C 2C,3G 3C,5G 3U,5G 4G 3C,4G     3C,4G      ##STR749##      0.05 3C 4C,8G 4C,9H 2C,9G 2C 0 0 1C 1C 2C 1C,2G 1H 1C,2G 1C,5H      ##STR750##      0.05 6Y,7C,9G 6C,9G 10C 6C,9G 1C,4G 2C,8G 2C 3C,7H 2C 2C,9G 2C,8H 2C,8G     2C,9G 2C,9H      ##STR751##      0.05 2B 0 1C,3G 1C 1C 0 0 0 0 0 0 1H 5G 2C,8H      ##STR752##      0.05 1B 3G 0 0 0 0 0 0 0 0 0 0 0 0      ##STR753##      0.05 6Y,1B,2H 4C,9G 3C,9G 3C,9H 2C 2C,5G 1C 2C,6H 0 0 2C,8H 2C,9G 1C,3G     1C,9G      ##STR754##      0.05 0 0 0 0 0 0 0 0 0 0 0 0 0 0      ##STR755##      0.05 3D,6Y 0 0 0 0 2G 0 2G 0 0 2C,7H 1H 8G 2C,9G      ##STR756##      0.4 9C 10C 10C 10C 9C 7C,9G 9C 9C 9C 9C 7U,9C 9C 8C 9C      ##STR757##      0.4 9C 9C 10C 10C 9C 9C 9C 9C 9C 9C 10C 9C 8C 10C      ##STR758##      0.4 9C 9C 10C 9C 9C 6C,9G 9C 9C 8C 4C,8G 5U,10C 6C,9G 5C,9G 6C,9G      ##STR759##      0.4 9C 9C 10C 9C 9C 9C 8C 9C 2C,8G 1C,5G 8U,9C 5C,9G 9C 2C,9G      ##STR760##      0.1 9C 9C 10C 10C 2C 1C 1C 3C 0 0 3C 9C 5C 2C      ##STR761##      0.05 7C,9G,6Y 6C,9G 10C 5C,9G 1C 9G 5G 4C,9H 2G 1C,6G 5C,9G 6H 8G 1C,9G      ##STR762##      0.4 9C 9C 10C 9C 9C 9C 9C 9C 9C 9C 6U,9C 9C 6C,9G 9C      ##STR763##      0.4 9C 9C 10C 9C 6C,9G 9C 9C 9C 9C 8C 5U,9C 9C 6C,9G 9C      ##STR764##      0.1 9C 9C 9C 3C 1C 2C 1C 9C 2C 1C 5C 9C 9C 5C      ##STR765##      1.0 0 0 0 0 0 0 0 0 0 0 0 0 0 0      ##STR766##      2.0 6C,9G,6Y 6C,9G 6C,9G 3C,9G 2C,7G 6C,7G 9C 10C 9C 9C 7U,9C 6C,9G     4C,9G 9C      ##STR767##      0.05 2C,4G,6Y 3C,3H,7G 9C 3C,9G 1C 2C,5G,5X 3G 3C,8H 2C 1C,2G 2C,8G     2H,9G,5X 8G 2H,9G      ##STR768##      0.05 3C,7G,6Y 3C,4H,9G 3C,9G 2C,9G 1C 2C,7G 1C 3C,9H 1C 1C 9H 2C,8G     8G,5I 9G,5I      ##STR769##      0.05 3C,8G,6Y 4C,3H,9G 9C 9C 1C 2C,7G 1C,5G 9C 1C 1C,2G 3H,9G 3H,9G,5X     9C 5C,9G      ##STR770##      0.05 1C 2C 1C 0 0 0 0 0 0 0 0 0 0 0      ##STR771##      0.05 5C,9G,6Y 5C,9G 4C,8G 10C, 1C,3H 2C,9G 1C 2C,9H 0 0 1C 2C,9G 2C,8G     2C,9H      ##STR772##      0.05 5C,9G,6Y 5C,9G 6C,9G 5C,9G 2C,4G 2C,9G 7G 9C 1C,6G 1C,6G 1C,4G     2C,2H,8G 5C,9G 4C,9G      ##STR773##      0.05 2C,9G,6Y 5C,9G 5C,9G 2H,9G 1C,5G 8G 2C,6G 2C,7H 0 0 1C,3G 0 6G     2C,9H      ##STR774##      0.05 1C,4G 2C,2H,8G 1C,5G 2G 1C,2G 1C,8G 1C,5G 1C,6G 0 1G 1C,2G 1H 8G     7H      ##STR775##      0.05 5C,9G,6Y 4C,7G 2C,7G 2C,9G 1C 4C,9G 9G 5C,9H 0 2C,9G 2C,9H 0 9G     1C,9G      ##STR776##      20.05 1C,1H0 00 00 00 00 00 4G0 6H0 00 00 00 1C0 00 2G0      ##STR777##      0.05 3C,5G,6Y 5C,9G 10C 5C,9G 2C,6G 9C 3C 2C,9H 0 2C 2C,7H 1C,5H 2C,8G     9H      ##STR778##      0.1 0 0 0 0 0 0 0 0 0 0 0 0 0 0      ##STR779##      0.05 2H 2C,7G 1C 5G 1C 2C,8G 0 3C,9H 0 0 2G 0 5G 9G      ##STR780##      2.0 2C 2C 0 0 0 0 0 0 0 0 0 0 0 0      ##STR781##      0.4 5S,7G,6Y 5C,9G 3C,8G 5C,9G 0 5G 2C,6G 5C,9H 0 0 2C,6H 0 1C,7G 1C,5H      ##STR782##      0.1 0 2G,2C,3H 5G,2C 8G 0 0 0 0 0 0 0 0 0 0      ##STR783##      0.1 10G,8C 10G,7C 10G,3C 10G 7G 0 0 3G 0 0 3G 10G,4C 10G,3C 9G      ##STR784##      0.1 10G,3C 10G,8C 10C 10C 9G 7G 0 5G 2G 2G 4G 10G,4H 1C,9G 7G      ##STR785##      0.05 10G,3H,2C  9G,4H,3C 10G,3C 10G,3H,2C 3G 9G,1C 4G 9G,5H 4G 6G       2     9G,2U,C 9G 10G,2C 10G      ##STR786##      0.05 9C 10C 9C 10C 1C 9C 9G 6C 1C 1C 3U 6C 5C 10C      ##STR787##      0.05 9C 9C 3C,9G 9C 1C,3G 9C 5C,9G 9C 3G 3C,9G 4U,9C 3C,9H 5C,9G 5U,9G      ##STR788##      0.05 3C,9G,6Y 5C,9G 2C,9G 9C 1C,3G 3G 2G 2C,9H 0 0 1U,9G 3H,8H 2C,9G     1U,9G      ##STR789##      0.05 9C 10C 9C 10C 2C 1C 2G 2C 0 0 2C 3C 2C 2C      ##STR790##      0.4 0 5C,8G 4C,9G 2H,7G 2C 0 2G 1H 0 0 2G 1G 3G 2G      ##STR791##      0.05 1C,5G,6Y 3C,5H,9G 2C,8G 6G 1C,4G 3G 2G 2C,6H 0 0 5H 0 3C,9G 2C,9G      ##STR792##      0.05 3C,9G,6Y 6C,9G 2C,9G 10C 1C,3G 2C,8G 4G 2C,9H 1C 1C 2C,8H 2C,6H 7G     2C,9G      ##STR793##      0.05 5C,9G,6Y 5C,9G 9C 2C,9G 1C,3G 2G 2G 5H 0 0 2G 2H,6G 6G 1H,7G      ##STR794##      0.05 5C,9G,6Y 6C,9G 6C,9G 6C,9G 1C,3G 2G 0 1H 0 0 2G 7H 5G 5G      ##STR795##      0.05 3C,8G,6Y 5C,9G 3C,9G 7G 1C 0 0 7H 0 0 0 0 0 6H      ##STR796##      0.05 3C,6Y -- 2C,9G 1C 1C 9G 6G 9H 0 2G 2C,8H 1C,2G 7G 9G      ##STR797##      0.05 2G,6F -- 0 0 0 0 0 0 0 0 0 0 0 0      ##STR798##      0.05 2C,5G,6Y 2C,3H,8G 2C 1C 1C,3G 5G 6G 3C,9H 0 0 1C 1C,3G 1C,7G 5C,9H      ##STR799##      0.05 0 -- 0 0 0 0 0 0 0 0 0 0 0 0      ##STR800##      0.05 2C,7G,6Y 5C,8G 4C,8G 3G 2C 5G 6G 5C,9H 4G 3G 3G 2C,2H 4C,9G 3C,9H      ##STR801##      0.05 0 -- 2C 0 1C 0 2H 1C 0 0 0 1H 0 1C      ##STR802##      0.05 3C,7G,6Y -- 2C,7G 2C,7H 1C 2C,7G 3C,8H 2C,9H 0 9G 2C,9H 2C 3C,9G     1C,9G      ##STR803##      0.1 1C,6Y 0 1C 2G 0 0 0 3H 0 0 0 0 0 2C,7G      ##STR804##      0.4 6C,9G,6Y 6C,9G 10C 10C 2C,5G 8G 9C 9C 4C,9G 4C,9G 5U,9G 2C,2H,8G     6C,9G 5U,9G      ##STR805##      0.05 2C,8G,6Y 3C,7G 2C,7G 2C,8G 1C 2G 0 0 0 0 3H 0 2C 2C,9H      ##STR806##      0.05 9C 9C 9C 9C 2C 9C 9C 10C 5C 9C 8U 10C 6C 5C      ##STR807##      0.05 9C 6C,9G 6C,9G 9C 3C,9G 5C,8G 5C,8G 10C 5C,9G 9C 7U,10C 6C,9G     5C,9G 10C      ##STR808##      0.05 9C 5C,9G 9C 9C 2C,3H 2C,7G 6G 6C,9H 0 0 7U,9H 9C 2C,7G 2C,9G      ##STR809##      2.0 4S,7G,6Y -- 0 0 0 0 0 0 0 0 0 0 0 0      ##STR810##      2.0 5S,9G,6Y -- 1C 0 0 0 2C 2C,5H 0 0 0 1C,4H 3G 2H      ##STR811##      2.0 5S,8G,6Y -- 2C,5G 2C,8H 2C 0 3G 1H 0 0 2H 2C,8G 4G 2G      PRE-EMERGENCE      ##STR812##      0.1   9G 9G 6G 10E 1C,7G 1C,9H 1C,6G 1C,9G 1C,9H 0 10E 10H      ##STR813##      0.1   9G 9H 8G 10E 1C,7G 1C,9H 1C,8G 1C,9G 9G 6H 10E 10E      ##STR814##      0.1   9G 9H 8G 10E 1C,8G 1C,9H 1C,8G 1C,9G 9G 6H 10E 1C,9H      ##STR815##      0.1   9G 8H 2C 0 0 1C,5G 0 0 1C,4G 0 10E 1C,9H      ##STR816##      0.4   5G 9G 2G 10E 3C 3C 0 0 1C,5H 1C,1H 10E 3C,9H      ##STR817##      0.1   9H 9H 6G 7G 5G 2C,7G 0 0 5G 2C,5H 10E 1C,7H      ##STR818##      0.1   9G 8H 8G 3G 2C 2C,8G 0 3G 1C,8G 2C,4G 9H 1C,9H      ##STR819##      0.4   5G,3C 6C,5G 4G 10E 4C,7G 5C,8G 3C,4G 10E  1C,3G 10E 7C,8G      ##STR820##      0.05   0 0 0 0 0 0 0 0 0 0 0 0      ##STR821##      0.05   9H 9H 5G 10E 1C 9H,3C 2C,7G 9G 1C,9H 1C,3H 4C,9H 2C,8H      ##STR822##      0.05   0 9H 2C 0 0 1C  0 1C,5G 0 2C 6H      ##STR823##      0.05   0 9H 0 0 0 0 0 0 0 0 0 0      ##STR824##      0.05   9G 5G 0 0 0 5H 0 0 1C,5C 2C,4H 1C,6G 2C      ##STR825##      0.05   0 0 0 0 0 0 0 0 0 0 0 0      ##STR826##      0.05   0 3C,8H 1H 0 0 1H 0 0 2G 3H 5G 6H      ##STR827##      0.4   9H 9H 10C 10E 10E 9H 5C,9H 10E 10E 9H 10E 10E      ##STR828##      0.4   9H 9H 9H 10E 10E 5C,9H 5C,9H 10E 10E 9H 10E 10E      ##STR829##      0.4   9G 9H 9G 9G 6C,9G 5C,9H 3C,9G 3C,9G 10E 9H 10E 6C,9H      ##STR830##      0.4   9H 9H 3C,9G 10E 3C,9H 5C,9H 3C,9G 1C,8H 3C,9H 9H 10E 6C,9H      ##STR831##      0.1   9G 9H 6G 10E 2G 3C,9H 2C,7G 1C,3G 3C,9G 9H 9H 4C,9G      ##STR832##      0.05   9G 9H 8G 10E 1C 2C,9H 1C,8G 1C,9C 1C,9G 1C,3G 10E 3C,9G      ##STR833##      0.4   9G 9H 6C,9G 10E 10E 3C,9H 2C,9H 10E 10E 9H 10E 2C,9G      ##STR834##      0.4   9G 9H 9G 9G 5C,9G 5C,9H 5C,9H 1C,9G 10E 9H 10E 10E      ##STR835##      0.1   9H 9H 9G 9G 2C,7G 5C,9H 3C,9G 9G 5C,9G 9H 10E 5C,9H      ##STR836##      1.0   0 0 0 0 0 0 0 0 0 0 0 0      ##STR837##      2.0   9C 9H 9G 10E 2C,9G 2C,9H 2C,9H 4C,9H 9H 9H 10E 5C,9H      ##STR838##      0.05   9G 9H 2G 2C,8G 1C 3C,8H 2C,5G 5G 1C,8G 2C,3G 8H 2C,9H      ##STR839##      0.05   8G 9H 4G 1C,8G 1C 9H,2C 2C,7G 2C,9G 2C,9H 8H 9H 1C,9G      ##STR840##      0.05   3C,9G 9H 5G 9G 2C,8G 9H 2C,8G 9H,2C 1C,9H 2C,6H 10E 7C,9H      ##STR841##      0.05   0 0 0 0 0 0 0 0 0 0 0 0      ##STR842##      0.05   8G 9H 0 9G 2C 2C,8H 1C,5G 1C,5G 2C,7G 1C 9H 2C,9H      ##STR843##      0.05   2C,9G 9H 6G,2C 2C,9G 3C,7G 5C,9H 2C,9G 1C,9G 2C,8G 2C,6H 10E     9C,9H      ##STR844##      0.05   9G 9H 0 9G 1C 2C,3G 1C 4G 2C,7G 0 2C,8H 2C,9G      ##STR845##      0.05   1H 8H 1H 9G 1C 3C,4G 3G 5G 6G 1H 8H 1C,7G      ##STR846##      0.05   5G 8H 0 10E 7G 2C,8G 2G 9G 2C,9H 0 10E 2C,9H      ##STR847##      20.05   6H0 6H0 00 00 2G0 00 00 00 00 00 1C0 2G0      ##STR848##      0.05   9H 9H 1C 8G 3C 3C,9H 2C 1C,4G 3C,7G 2G 2C,9H 2C,9H      ##STR849##      0.1   0 0 0 0 0 0 0 0 0 0 0 0      ##STR850##      0.05   2G 9H 0 8G 0 7H 0 3G 2C,6G 0 3C,9H 9H      ##STR851##      2.0   6G 8H 0 0 0 4C 0 0 2C 0 0 2G      ##STR852##      0.4   8G 9H 2C 0 0 1C 0 0 2C 1C 5H 2C      ##STR853##      0.1   5G 5G 0 0 0 0 0 0 0 0 4G 2G      ##STR854##      0.1   9G 10E 8G 6G 3G 5G 0 4G 4G 9G 7G 6G      ##STR855##      0.1   9G 6G 8G 5G 1G 3G 2G 2G 2G 9G 7G 6G      ##STR856##      0.05   9G 7G 7G 9G 3G 3H,9G 6G 7G 9G 1G,2C 7G 9G      ##STR857##      0.05   3C,9G 9H 6G 10E 5G 2C,9H 2C,9G 2C,9G 1U,9H 9H 10E 10H      ##STR858##      0.05   9H -- 5G 10E 8G 2C,9H 2C,5G 9H 10E 1C,7H 10E 4C,9H      ##STR859##      0.05   8H 9H 4G 0 0 2C,6H 0 3G 1C,9G 1C,5H 10E 2C,9H      ##STR860##      0.05   10C -- 2C,9G 2C 1C 3C,9H 1C,4G 1C,4G 9G 2C,9H 10E 2C,9H      ##STR861##      0.4   5G 9H 0 4G 0 0 0 0 4G 0 2C,8G 3H      ##STR862##      0.05   7G 9G 3G 9G 0 2C 0 3G 1C,6G 0 2C,6G 2C      ##STR863##      0.05   8G 9H 1C,3G 10E 2C 3C,7H 1C,4G 1C,5G 2C,8H 2H 3C,7G 2C,9H      ##STR864##      0.05   9G 2C,9H 6G 2G 1C 0 0 0 1C,3G 1C,3G 1C 2C      ##STR865##      0.05   9G 9H 2C,6G 1C,7G 1C,4G 1C,3H 2C 0 2C,5G 2C,5H 2C,4G 1C,3G      ##STR866##      0.05   5G 3H 0 0 0 5H,2C 0 0 2G 0 2C,4G 2C,5G      ##STR867##      0.05   8H 9H 2C 10E 3G 2C,6G 2G 8G 8H 0 9H 3C,9H      ##STR868##      0.05   0 0 1C 0 2G 1C 0 0 2G 2G 5G 1C      ##STR869##      0.05   5G,3C 7H 2C 8G 1C,3G 2C,4G 1C 3G 1C,4G 2G 5C,9H 4C,8G      ##STR870##      0.05   1C 2G 0 0 0 0 0 0 0 0 0 0      ##STR871##      0.05   10E 10E 1C 5G 5G 5G 3G 4G 1C,4G 3G 3C,9H 3C,9H      ##STR872##      0.05   0 2G 0 0 0 2H 2G 2G 1C,2G 0 2G 1C,5G      ##STR873##      0.05   8G 9H 0 4G 1C 3C,9H 3G 2C,7G 9G 0 10E 1C,9G      ##STR874##      0.1   0 0 0 0 0 0 0 0 0 0 0 0      ##STR875##      0.4   9H -- 7G 2C,7G 5C,9G 6C,9H 3C,9G 2C,9G 2C,9H 1C,2H 10E 5C,9H      ##STR876##      0.05   0 8H 0 0 0 0 0 0 2C,5G 0 7H 2C,8H      ##STR877##      0.05   9C 9H 9G 10E 5C,9G 5C,9H 2C,8G 10E 10E 3C,9H 10E 10E      ##STR878##      0.05   9C 9H 9G 10E 5C,9G 2C,9H 2C,9G 10E 10E 9H 10E 10E      ##STR879##      0.05   9C 9H 3C,9G 8G 5G 5C,9H 2C,4G 1C,6G 2C,9H 9H 10E 5C,9H      ##STR880##      2.0   0 0 0 0 0 0 0 0 0 0 0 0      ##STR881##      2.0   5G -- 1C 0 3G 0 0 0 0 0 0 0      ##STR882##      2.0   5G 8H 3H 0 1C 2C 0 0 2G 0 2C,5H 1C,3G

TEST B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinum), mustard (Brassica arvensis), cocklebur(Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus),morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared oil and planted with rice and wheat. Another 12.5 pot wasplanted with sugarbeets. The above four containers were treatedpreemergence with certain test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B. Note that certain compounds are useful as pre-emergencetreatments for weed control in crops such as soybeans and wheat.

                  TABLE B                                                         ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                        ______________________________________                                                 ##STR883##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    8G, 7C         10E                                               Barnyardgrass                                                                              7G, 3H         8G, 9C                                            Sorghum      10E            10E                                               Wild Oats    2G             5G                                                Johnsongrass 7G, 3H         8G, 5H                                            Dallisgrass  3G             4G                                                Giant foxtail                                                                              8G, 8C         9G, 9C                                            Ky. bluegrass                                                                              --             --                                                Cheatgrass   8G             7G                                                Sugarbeets   8G, 6C         8G, 7C                                            Corn         5G, 5H         7G, 5H                                            Mustard      8G, 8C         9G, 9C                                            Cocklebur    6G, 3H         6G, 3H                                            Pigweed      10C            10C                                               Nutsedge     7G             8G                                                Cotton       8G             8G                                                Morningglory 7G             8G                                                Cassia       3G             3G                                                Teaweed      5G             6G                                                Velvetleaf   6G, 3H         7G, 5C                                            Jimsonweed   6G, 6C         6G, 6C                                            Soybean      0              4G                                                Rice         10E            10E                                               Wheat        3G, 3C         4G, 3C                                            ______________________________________                                                 ##STR884##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    7G, 5C         10C                                               Barnyardgrass                                                                              7G, 6C         8G, 9C                                            Sorghum      10E            10E                                               Wild Oats    5G             7G                                                Johnsongrass 6G, 5H         9G, 8C                                            Dallisgrass  7G             8G                                                Giant foxtail                                                                              6G, 3C         9G, 3C                                            Ky. bluegrass                                                                              --             --                                                Cheatgrass   8G             10E                                               Sugarbeets   8G, 7C         8G, 7C                                            Corn         5G, 5H         4G, 3H                                            Mustard      9G, 9C         9G, 9C                                            Cocklebur    7G, 4C         6G, 5H                                            Pigweed      9G, 9C         10C                                               Nutsedge     7G             9G                                                Cotton       8G             8G                                                Morningglory 7G             8G                                                Cassia       3G             4G                                                Teaweed      4G             5G, 2C                                            Velvetleaf   7G, 7C         10C                                               Jimsonweed   5G             5G, 3C                                            Soybean      0              6G, 4C                                            Rice         10E            10E                                               Wheat        7G, 4C         7G, 4C                                            ______________________________________                                                 ##STR885##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    3G             4H                                                Barnyardgrass                                                                              3G             5H                                                Sorghum      3G             5G, 3H                                            Wild Oats    0              0G                                                Johnsongrass 0              4G, 3H                                            Dallisgrass  3G             4G                                                Giant foxtail                                                                              0              3G                                                Ky. bluegrass                                                                              0              5G                                                Cheatgrass   3G             5G                                                Sugarbeets   0              3G                                                Corn         2C             2C, 2U                                            Mustard      5G             7G                                                Cocklebur    0              0                                                 Pigweed      3G             4G                                                Nutsedge     0              0                                                 Cotton       0              3G                                                Morningglory 3G             5G                                                Cassia       0              0                                                 Teaweed      0              0                                                 Velvetleaf   0              0                                                 Jimsonweed   0              0                                                 Soybean      0              0                                                 Rice         5G, 3C         7G, 8C                                            Wheat        0              3G                                                ______________________________________                                                 ##STR886##                                                           Rate kg/ha   0.03       0.12       0.007                                      ______________________________________                                        Crabgrass    8G         9G, 8C     6G                                         Barnyardgrass                                                                              9G, 7C     9G, 7C     9G, 9C                                     Sorghum      10E        10E        8G, 9C                                     Wild Oats    6G, 3H     8G, 8C     6G, 3H                                     Johnsongrass 8G, 3C     9G, 9C     8G, 5C                                     Dallisgrass  --         --         5G                                         Giant foxtail                                                                              6G, 3H     9G, 8C     3G                                         Ky. bluegrass                                                                              7G, 7C     8G, 9C     7G                                         Cheatgrass   10E        10E        10E                                        Sugarbeets   9G, 9C     9G, 9C     7G, 6C                                     Corn         7G, 5H     9G, 9C     5G, 2C                                     Mustard      9G, 9C     9G, 9C     8G, 8C                                     Cocklebur    6G, 3H     7G, 5H     6G                                         Pigweed      9G, 8C     10E        10C                                        Nutsedge     7G         6G         6G                                         Cotton       7G         8G, 3C     2G                                         Morningglory 8G, 3C     9G, 8C     7G                                         Cassia       7G         7G         5G                                         Teaweed      6G         7G         2G                                         Velvetleaf   8G, 3C     10C        9G, 5H                                     Jimsonweed   7G         8G, 4C     4G                                         Soybean      4G         7G, 5H     2G                                         Rice         10E        10E        9G, 9C                                     Wheat        6G, 3H     8G, 8C     6G                                         ______________________________________                                                 ##STR887##                                                           Rate kg/ha   0.03       0.12       0.007                                      ______________________________________                                        Crabgrass    8G         9G, 8C     7G                                         Barnyardgrass                                                                              9G, 8C     9G, 9C     9G, 8G                                     Sorghum      10E        10E        9G, 9C                                     Wild Oats    7G, 3H     8G, 8C     6G, 4G                                     Johnsongrass 8G, 3C     10C        8G, 3C                                     Dallisgrass  --         --         5G                                         Giant foxtail                                                                              9G, 5H     10C        5G, 2C                                     Ky. bluegrass                                                                              9G, 9C     10C        8G                                         Cheatgrass   10E        10E        10E                                        Sugarbeets   9G, 9C     9G, 9C     7G, 8C                                     Corn         7G, 5H     9G, 9C     7G, 3H                                     Mustard      9G, 9C     10C        7G, 8C                                     Cocklebur    6G         8G, 5H     4G                                         Pigweed      10E        10E        9G, 9C                                     Nutsedge     5G         7G         5G                                         Cotton       7G, 3H     9G, 8C     4G, 2H                                     Morningglory 8G, 3C     9G, 6C     7G, 3C                                     Cassia       7G         7G         4G                                         Teaweed      7G         7G, 5C     4G                                         Velvetleaf   8G, 6C     10C        8G, 5H                                     Jimsonweed   7G, 5C     9G, 9C     4G                                         Soybean      7G, 5H     8G, 5H     3G                                         Rice         10E        10E        9G, 9C                                     Wheat        6G         8G, 8C     5G                                         ______________________________________                                                 ##STR888##                                                           Rate kg/ha   0.03       0.12       0.007                                      ______________________________________                                        Crabgrass    7G, 3C     9G, 9C     2G                                         Barnyardgrass                                                                              6G, 3C     7G, 3C     4G                                         Sorghum      8G, 3C     10C        8G, 3H                                     Wild Oats    4G         6G         2G                                         Johnsongrass 8G, 4C     8G, 4C     4G                                         Dallisgrass  0          5G         0                                          Giant foxtail                                                                              0          7G, 3H     0                                          Ky. bluegrass                                                                              8G, 8C     8G, 8C     0                                          Cheatgrass   5G         7G, 3H     3G                                         Sugarbeets   9G, 9C     10C        10C                                        Corn         9G, 7C     9G, 9C     7G, 3H                                     Mustard      10C        10C        10C                                        Cocklebur    8G, 5H     9G, 5H     6G                                         Pigweed      9G, 9C     10C        9G, 9C                                     Nutsedge     6G         6G         3G                                         Cotton       8G, 5H     8G, 5H     6G, 3H                                     Morningglory 8G, 3H     9G, 5H     9G, 8C                                     Cassia       9G, 8C     --         7G                                         Teaweed      7G, 3C     7G, 3C     4G                                         Velvetleaf   9G, 9C     10C        9G, 8G                                     Jimsonweed   6G, 5C     7G, 7C     5G                                         Soybean      9G, 5H     9G, 5H     6G, 9H                                     Rice         10E        10E        6G                                         Wheat        4G         4G         0                                          ______________________________________                                                 ##STR889##                                                           Rate kg/ha   0.03       0.12       0.007                                      ______________________________________                                        Crabgrass    3G         6G, 3C, 0                                             Barnyardgrass                                                                              5G         7G, 4C     4G                                         Sorghum      8G, 3H     9G, 9C     7G, 3H                                     Wild Oats    2G         4G         0                                          Johnsongrass 5G, 3H     7G, 3H     5G                                         Dallisgrass  0          6G         2G                                         Giant foxtail                                                                              0          3G         0                                          Ky. bluegrass                                                                              6G         8G, 8C     3G                                         Cheatgrass   0          7G         0                                          Sugarbeets   10C        9G, 9C     9G, 9C                                     Corn         6G, 3H     6G, 5H     2G, 1U                                     Mustard      10C        10C        10E                                        Cocklebur    6G         7G, 5H     6G                                         Pigweed      8G, 8C     10C        7G, 5E                                     Nutsedge     2G         7G         6G                                         Cotton       6G, 5H     9G, 5H     6G, 3H                                     Morningglory 8G, 3H     8G, 3H     9G, 8C                                     Cassia       6G         --         4G                                         Teaweed      6G, 2C     7G, 3C     3G                                         Velvetleaf   8G, 5H     8G, 8C     6G                                         Jimsonweed   5G         6G, 3C     5G                                         Soybean      5G         9G, 5H     4G, 3H                                     Rice         7G         10E        5G                                         Wheat        2G         2G         0                                          ______________________________________                                                 ##STR890##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    0              0                                                 Barnyardgrass                                                                              3G             3G                                                Sorghum      0              6G, 3H                                            Wild Oats    0              0                                                 Johnsongrass 0              5G, 3H                                            Dallisgrass  0              3G                                                Giant foxtail                                                                              0              2H                                                Ky. bluegrass                                                                              4G             6G                                                Cheatgrass   0              10E                                               Sugarbeets   3G             3G                                                Corn         0              0                                                 Mustard      8G, 5C         10C                                               Cocklebur    0              0                                                 Pigweed      4G             8G, 8C                                            Nutsedge     0              7G                                                Cotton       0              3G                                                Morningglory 3G             4G                                                Cassia       0              0                                                 Teaweed      0              3G                                                Velvetleaf   5G, 3H         6G, 3H                                            Jimsonweed   3G             5G                                                Soybean      0              2G                                                Rice         4G             5G, 3H                                            Wheat        0              0                                                 ______________________________________                                                 ##STR891##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    0              0                                                 Barnyardgrass                                                                              6G             6G, 5H                                            Sorghum      7G, 3H         10C                                               Wild Oats    3G             3G                                                Johnsongrass 6G, 3H         8G, 5E                                            Dallisgrass  0              4G                                                Giant foxtail                                                                              0              3G                                                Ky. bluegrass                                                                              7G, 4C         7G, 4C                                            Cheatgrass   7G, 5C         9G, 9C                                            Sugarbeets   6G, 3H         10C                                               Corn         4G, 2U         6G, 5H                                            Mustard      10C            10C                                               Cocklebur    2G             3G                                                Pigweed      8G, 8C         10C                                               Nutsedge     7G             7G                                                Cotton       5G             5G, 2H                                            Morningglory 5G             4G                                                Cassia       5G             5G                                                Teaweed      2G             4G                                                Velvetleaf   8G, 5H         9G, 5H                                            Jimsonweed   8G             8G                                                Soybean      4G             4G                                                Rice         7G             8G                                                Wheat        4G             6G                                                ______________________________________                                                 ##STR892##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    8G, 5C         9G, 7C                                            Barnyardgrass                                                                              9G, 7C         9G, 7C                                            Sorghum      10E            10E                                               Wild Oats    7G, 3C         8G, 5E                                            Johnsongrass 9G, 7C         9G, 9C                                            Dallisgrass  7G             8G                                                Giant foxtail                                                                              7G, 3H         9G, 5H                                            Ky. bluegrass                                                                              10C            9G, 9C                                            Cheatgrass   10C            10E                                               Sugarbeets   9G, 9C         9G, 9C                                            Corn         7G, 5H         8G, 3C                                            Mustard      10C            10E                                               Cocklebur    6G             7G                                                Pigweed      10E            10E                                               Nutsedge     8G             10E                                               Cotton       3G             7G, 5H                                            Morningglory 6G             8G, 3H                                            Cassia       5G             7G                                                Teaweed      6G             8G, 5C                                            Velvetleaf   8G, 7C         10C                                               Jimsonweed   6G             7G, 7C                                            Soybean      3G             6G, 3H                                            Rice         10E            10E                                               Wheat        7G, 3C         7G, 5C                                            ______________________________________                                                 ##STR893##                                                           Rate kg/ha   0.03       0.12       0.007                                      ______________________________________                                        Crabgrass    7G, 3H     8G, 5C     0                                          Barnyardgrass                                                                              6G, 3H     8G, 4C     0                                          Sorghum      9G, 9C     10E        5G, 3H                                     Wild Oats    2G         7G, 3H     0                                          Johnsongrass 8G, 5H     8G, 5C     0                                          Dallisgrass  6G         0          0                                          Giant foxtail                                                                              7G, 7C     7G, 7C     0                                          Ky. bluegrass                                                                              7G, 7C     7G, 5C     0                                          Cheatgrass   7G, 3C     10C        0                                          Sugarbeets   9G, 9C     9G, 9C     5G, 3H                                     Corn         10C        10E        3G                                         Mustard      10C        10C        7G, 3C                                     Cocklebur    7G, 5H     8G, 5H     2G                                         Pigweed      10C        10C        5G                                         Nutsedge     6G         7G         0                                          Cotton       7G         8G, 5H     0                                          Morningglory 8G, 3H     8G, 3H     6G, 5H                                     Cassia       6G         --         0                                          Teaweed      6G         7G, 4C     0                                          Velvetleaf   8G, 8C     8G, 8C     3G                                         Jimsonweed   6G, 4C     6G, 5C     0                                          Soybean      2H         7G, 5H     0                                          Rice         10E        10E        7G, 3H                                     Wheat        5G         6G         0                                          ______________________________________                                                 ##STR894##                                                           Rate kg/ha   0.03           0.12                                              ______________________________________                                        Crabgrass    0              5G                                                Barnyardgrass                                                                              5G, 3H         4G, 2H                                            Sorghum      8G, 5H         10C                                               Wild Oats    0              3C                                                Johnsongrass 7G, 3H         8G, 5H                                            Dallisgrass  0              4G                                                Giant foxtail                                                                              0              4H                                                Ky. bluegrass                                                                              7G             8G, 8C                                            Cheatgrass   10E            10E                                               Sugarbeets   6G, 3H         10C                                               Corn         5G, 3H         6G, 5H                                            Mustard      8G, 5C         10C                                               Cocklebur    0              5G                                                Pigweed      5G             10E                                               Nutsedge     0              5G                                                Cotton       3G             6G, 3H                                            Morningglory 4G             5G                                                Cassia       3G             3G                                                Teaweed      3G             4G, 2C                                            Velvetleaf   3H             6G, 3H                                            Jimsonweed   3G             7G, 3C                                            Soybean      0              4G, 3H                                            Rice         6G             7G, 5H                                            Wheat        3G             3G                                                ______________________________________                                                 ##STR895##                                                           Rate kg/ha   0.12           0.5                                               ______________________________________                                        Crabgrass    0              0                                                 Barnyardgrass                                                                              0              0                                                 Sorghum      0              7G, 5H                                            Wild Oats    0              4G                                                Johnsongrass 0              5G                                                Dallisgrass  0              3G                                                Giant Foxtail                                                                              0              2G                                                Ky. bluegrass                                                                              --             --                                                Cheatgrass   0              5G                                                Sugarbeets   2G             6G                                                Corn         0              4G                                                Mustard      8G, 5C         10C                                               Cocklebur    6G, 3C         6G, 2C                                            Pigweed      4G, 4C         7G, 7C                                            Nutsedge     0              5G                                                Cotton       3G             7G                                                Morningglory 0              6G                                                Cassia       0              3G                                                Teaweed      0              0                                                 Velvetleaf   4G, 3C         5G                                                Jimsonweed   0              0                                                 Soybean      0              4G, 2H                                            Rice         0              2G                                                Wheat        0              3G                                                ______________________________________                                                 ##STR896##                                                           Rate kg/ha   0.06       0.12       0.5                                        ______________________________________                                        Crabgrass    6G, 7C     4G         7G                                         Barnyardgrass                                                                              4          6          8G, 4C                                     Sorghum      9G, 5C     9G, 8C     10C                                        Wild Oats    0          0          0                                          Johnsongrass 4G, 3H     4G         7G, 3H                                     Dallisgrass  0          0          3G                                         Giant foxtail                                                                              3G         3          6G, 3C                                     Ky. bluegrass                                                                              3G         3          5G                                         Cheatgrass   3G         --         --                                         Sugarbeets   9G, 9C     10C        10C                                        Corn         5G         6G, 3H     9G, 5H                                     Mustard      10C        8G         10C                                        Cocklebur    6G, 3H     7G, 3H     8G, 5H                                     Pigweed      8G, 8C     10C        10E                                        Nutsedge     3G         7G         8G                                         Cotton       8G, 3H     9G, 5C     9G, 5C                                     Morningglory 8G, 3H     8G, 3H     9G, 9C                                     Cassia       6G         5G         7G                                         Teaweed      5G, 3H     4G         8G, 5C                                     Velvetleaf   8G, 7C     10C        10C                                        Jimsonweed   9G, 9C     7G         10C                                        Soybean      0          3G         5G, 3H                                     Rice         10E        8G, 6C     10E                                        Wheat        0          0          0                                          ______________________________________                                    

WHEAT AND BARLEY HERBICIDE SCREEN

Two ten-inch in diameter plastic pans lined with polyethylene linerswere filled with prepared Fallsington silt loam soil. One pan wasplanted with seeds of wheat (Triticum aestivum), barley (Hordeumvulgare), wild oats (Avena fatua), downy brome (Bromus tectorum),cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides),annual bluegrass (Poa annua), green foxtail (Setaria viridis),quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) andripgut brome A(Bromus rigidus). The other pan was planted with seeds ofRussian thistle (Salsola kali), tansy mustard (Descuraina pinnata),smartweed (Polygonum pennsylvanicum), tumble mustard (Sisymbriumaltissium), kochia (Kochia scoparia), shepherd's purse (Capsellabursa-pastoris), Matricaria indora, black nightshade (Solanum nigrum),yellow rocket (Barbarea vulgaris), wild mustard (Brassica kaber) andwild buckwheat (Polygonum convolvulus). The above two pans were treatedpre-emergence. At the same time two pans in which the above plantspecies were growing were treated post-emergence. Plant height at thetime of treatment ranged from 1-15 cm depending on plant species.

The compounds applied were diluted with a non-pytotoxic solvent andsprayed over-the-top of the pans. An untreated control and a solventalone control were included for comparison. All treatments weremaintained in the greenhouse for 20 days at which time the treatmentswere compared to the controls and the effects visually rated. Therecorded data are presented in Table C. It will be seen that thecompounds have utility for selective weed control in cereal crops.

                  TABLE C                                                         ______________________________________                                         ##STR897##                                                                            Post-emergence                                                                             Pre-emergence                                           Rate kg/ha 0.008      0.03    0.008    0.03                                   ______________________________________                                        wheat      1C,1G      6C,5G   0        0                                      barley     2C,3G      1G      1G       2G                                     wild oats  7C,5G      1C,1G   0        0                                      downy brome                                                                              7C,7G      2G      2G       10C                                    cheatgrass 10C        1C,4G   7G       10C                                    blackgrass 9C,8G      3C,3G   5G       7C,7G                                  annual bluegrass                                                                         10C        8C,8G   3C,6G    7C,8G                                  green foxtail                                                                            10C        1C,3G   1C,2G    5C,6G                                  quackgrass 2C,3G      10C     3G       2C,5G                                  Italian ryegrass                                                                         6C,7G      10C     1C,5G    1C,3G                                  ripgut brome                                                                             1C,2G      3C,4G   0        1C,3G                                  Russian thistle                                                                          10C        10C     3G       7C,6G                                  tansy mustard                                                                            10C        10C     10C      10C                                    smartweed  --         --      --       --                                     jimhill mustard                                                                          10C        10C     10C      10C                                    Kochia     10C        10C     10C      10C                                    shepherd's purse                                                                         10C        10C     10C      10C                                    false chamomile                                                                          10C        10C     10C      6C,7G                                  black nightshade                                                                         10C        10C     7G       7C,8G                                  yellow rocket                                                                            10C        10C     10C      10C                                    wild mustard                                                                             10C        10C     10C      10C                                    wild buckwheat                                                                           10C        7C,6G   10C      10C                                    ______________________________________                                                  ##STR898##                                                                     Post-emergence Pre-emergence                                       Rate kg/ha 0.015          0.015                                               ______________________________________                                        wheat      0              0                                                   barley     0              0                                                   wild oats  0              2C,2G                                               downy brome                                                                              0              1C,3G                                               cheatgrass 0              1C,4G                                               blackgrass 0              3G                                                  annual bluegrass                                                                         0              2G                                                  green foxtail                                                                            0              0                                                   quackgrass 0              0                                                   Italian ryegrass                                                                         0              0                                                   ripgut brome                                                                             0              0                                                   Russian thistle                                                                          10C            0                                                   tansy mustard                                                                            10C            10C                                                 smartweed  --             --                                                  jimhill mustard                                                                          10C            10C                                                 Kochia     10C            2C,5G                                               shepherd's purse                                                                         10C            10C                                                 false chamomile                                                                          10C            4C,6G                                               black nightshade                                                                         0              2C,6G                                               yellow rocket                                                                            10C            3C,8G                                               wild mustard                                                                             10C            9C,9G                                               wild buckwheat                                                                           3C,2G          4G                                                  ______________________________________                                                  ##STR899##                                                                     Post-emergence Pre-emergence                                       Rate kg/ha 0.06           0.06                                                ______________________________________                                        wheat      2G             0                                                   barley     0              0                                                   wild oats  0              3C,4G                                               downy brome                                                                              0              4C,6G                                               cheatgrass 7C,5G          10C                                                 blackgrass 7C,7G          10C                                                 annual bluegrass                                                                         2G             3C,5G                                               green foxtail                                                                            1C,3G          2C,4G                                               quackgrass 0              2C,3G                                               Italian ryegrass                                                                         0              0                                                   ripgut brome                                                                             0              0                                                   Russian thistle                                                                          10C            7C,8G                                               tansy mustard                                                                            10C            10C                                                 smartweed  --             --                                                  jimhill mustard                                                                          10C            10C                                                 Kochia     10C            7C,7G                                               shepherd's purse                                                                         10C            10C                                                 false chamomile                                                                          10C            7C,9G                                               black nightshade                                                                         0              2C,7G                                               yellow rocket                                                                            10C            9C,9G                                               wild mustard                                                                             10C            10C                                                 wild buckwheat                                                                           7C,6G          2C,7G                                               ______________________________________                                                  ##STR900##                                                                   Post-emergence                                                                             Pre-emergence                                           Rate kg/ha 0.015      0.06    0.015    0.06                                   ______________________________________                                        wheat      0          0       0        0                                      barley     0          0       0        0                                      wild oats  0          0       0        0                                      downy brome                                                                              0          2C,3G   2G       2C,3G                                  cheatgrass 0          2C,5G   1G       1C,5G                                  blackgrass 0          1C,3G   3G       2C,7G                                  annual bluegrass                                                                         0          1C,4G   2G       2C,3G                                  green foxtail                                                                            0          2G      0        2C,3G                                  quackgrass 0          0       0        1C,2G                                  Italian ryegrass                                                                         0          3G      0        3G                                     ripgut brome                                                                             0          0       0        0                                      Russian thistle                                                                          10C        10C     2C,2G    7C,8G                                  tansy mustard                                                                            10C        10C     10C      10C                                    smartweed  --         --      --       --                                     jimhill mustard                                                                          10C        10C     10C      10C                                    Kochia     2C,4G      7C,7G   3C,5G    7C,7G                                  shepherd's purse                                                                         10C        10C     10C      10C                                    false chamomile                                                                          10C        10C     7C,8G    9C,9G                                  black nightshade                                                                         1C,3G      3C,6G   1C,8G    2C,8G                                  yellow rocket                                                                            2C,3G      10C     5C,6G    6C,8G                                  wild mustard                                                                             10C        10C     9C,9G    9C,9G                                  wild buckwheat                                                                           9C,8G      10C     4C,7G    7C,7G                                  ______________________________________                                                  ##STR901##                                                                   Post-emergence                                                                             Pre-emergence                                           Rate kg/ha 0.008      0.03    0.008    0.03                                   ______________________________________                                        wheat      0          0       0        0                                      barley     0          0       0        0                                      wild oats  0          0       0        0                                      downy brome                                                                              0          1G      1C,2G    2C,5G                                  cheatgrass 0          2G      3G       2C,5G                                  blackgrass 1G         1C,3G   1C,3G    5C,7G                                  annual bluegrass                                                                         1G         3G      5C,6G    5C,7G                                  green foxtail                                                                            2G         2C,3G   0        3G                                     quackgrass 0          1G      2G       2C,7G                                  Italian ryegrass                                                                         0          2G      4G       1G                                     ripgut brome                                                                             0          0       0                                               Russian thistle                                                                          10C        10C     4C,5G    10C                                    tansy mustard                                                                            10C        10C     10C      10C                                    smartweed  --         --      --       --                                     jimhill mustard                                                                          10C        10C     10C      10C                                    Kochia     8C,8G      10C     7C,8G    8C,9G                                  shepherd's purse                                                                         9C,8G      10C     10C      10C                                    false chamomile                                                                          10C        10C     10C      9C,9G                                  black nightshade                                                                         1G         2C,3G   2C,5G    3C,8G                                  yellow rocket                                                                            10C        10C     10C      10C                                    wild mustard                                                                             10C        10C     10C      10C                                    wild buckwheat                                                                           8C,7G      10C     4C,7G    8C,8G                                  ______________________________________                                    

What is claimed is:
 1. A compound selected from ##STR902## wherein W isoxygen or sulfur;W' is oxygen or sulfur; A' is H, Cl, Br, C₁ -C₄ alkyl,OCH₃, NO₂ or CF₃ ' R^(I) is C₁ -C₆ alkyl; C₃ -C₆ alkenyl; C₃ -C₆alkynyl; C₂ -C₆ alkyl substituted with Cl, CN or OCH₃ ; C₃ -C₆ alkenylsubstituted with 1-3 Cl; C₃ -C₆ alkynyl substituted with Cl; C₃ -C₆cycloalkyl; cyclohexenyl; cyclohexyl substituted with 1-3 CH₃ ; C₄ -C₇cycloalkylalkyl or ##STR903## where R₇ and R₈ are independently H, Cl,CH₃ or OCH₃ ; n is 0 or 1; and R₉ is H or CH₃ ; CH₂ CH₂ OR₁₅, CH₂ CH₂CH₂ OR₁₅, ##STR904## where R₁₅ is C₂ H₅, CH(CH₃)₂, phenyl, CH₂ CH₂ Cl,CH₂ CCl₃ ; --CH₂ CH₂ O--_(n) 'R₁₆, ##STR905## where R₁₆ is CH₃, C₂ H₅,CH(CH₃)₂, phenyl, CH₂ CH₂ Cl, CH₂ CCl₃, and n' is 2 or 3; CH₂ CN;##STR906## where R₆ ' is C₁ -C₄ alkyl; provided R^(I) has a total of ≦13carbon atoms.